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【结 构 式】 
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【分子编号】41907 【品名】(3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 【CA登记号】20031-21-4 |
【 分 子 式 】C8H14O5 【 分 子 量 】190.19616 【元素组成】C 50.52% H 7.42% O 42.06% |
合成路线1
该中间体在本合成路线中的序号：(I)Finally this compound can be deprotected by conventional methods: (a) The acylation of 1,2-O-isopropylidene-alpha-D-xylofuranose (I) with benzoyl chloride and pyridine gives the 5-O-benzoyl derivative (II), which is acylated again with Ac2O in pyridine to yield the 3-O-acetyl-5-O-benzoyl derivative (III). The reaction of (III) with Ac2O in acetic acid affords the triacetyl derivative (IV) which is condensed with fully silylated thymine (V) by means of SnCl4 in acetone to provide the corresponding adduct (VI). The selective hydrolysis of the acetate groups of (VI) with sulfuric acid in hot acetonitrile gives 1-(5-O-benzoyl-beta-D-xylofuranosyl)thymine (VII), which is treated with MsCl and pyridine to yield the dimesylate (VIII). The reaction of (VIII) with NaI in refluxing dimethoxyethane affords, after column chromatography, 5'-O-benzoyl-3'-deoxy-2',3'-dideoxythymidine (IX), which is finally deprotected with NaOMe in methanol. (b) The reaction of the 5-O-benzoyl derivative (II) with MsCl and pyridine gives the mesylate (X), which is acylated with Ac2O in HOAc to yield 1,2-di-O-acetyl-5-O-benzoyl-3-O-(methylsulfonyl)-alpha-D-xylofuranose (XI). The condensation of (XI) with the fully silylated thymine (V) by means of SnCl4 in acetone affords the expected adduct (XII), which is treated with H2SO4 in hot MeCN to provide 1-(5'-O-benzoyl-3'-O-(methylsulfonyl)-beta-D-xylofuranosyl)thymine (XIII). Finally this compound is treated with MsCl and pyridine to yield the dimesylate (VIII), already reported. (c) The 1-(5-O-benzoyl-beta-D-xylofuranosyl)thymine (VII) can also be treated with TsCl and pyridine to give the ditosylate (XIV), which is then treated with NaI in refluxing dimethoxyethane to yield 5'-O-benzoyl-3'-deoxy-2',3'-dideoxythymidine (IX), already reported.
| 【1】 Spirikhin, L.V.; Mustafin, A.G.; Tolstikov, G.A.; Abdrakhumanov, L.B.; Gataullin, R.R.; Transformations of beta-D-xylofuranosyl nucleosides. Synthesis of 3'-deoxy-2,3-didehydrothymidine (D4T). Russian J Org Chem 1996, 32, 12, 1787. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 41907 | (3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | 20031-21-4 | C8H14O5 | 详情 | 详情 |
| (II) | 41908 | [(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate | C15H18O6 | 详情 | 详情 | |
| (III) | 41909 | [(3aR,5R,6S,6aR)-6-(acetoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate | C17H20O7 | 详情 | 详情 | |
| (IV) | 41910 | [(2R,3S,4R,5R)-3,4,5-tris(acetoxy)tetrahydro-2-furanyl]methyl benzoate | C18H20O9 | 详情 | 详情 | |
| (V) | 41900 | 5-methyl-2,4-bis[(trimethylsilyl)oxy]pyrimidine; 5-methyl-2-[(trimethylsilyl)oxy]-4-pyrimidinyl trimethylsilyl ether | 7288-28-0 | C11H22N2O2Si2 | 详情 | 详情 |
| (VI) | 41911 | [(2R,3S,4R,5R)-3,4-bis(acetoxy)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C21H22N2O9 | 详情 | 详情 | |
| (VII) | 41912 | [(2R,3R,4R,5R)-3,4-dihydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C17H18N2O7 | 详情 | 详情 | |
| (VIII) | 41913 | [(2R,3S,4R,5R)-3,4-bis[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C23H30N2O7S2 | 详情 | 详情 | |
| (IX) | 12254 | [(2S,5R)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl benzoate | C17H16N2O5 | 详情 | 详情 | |
| (X) | 41914 | ((3aR,5R,6S,6aR)-2,2-dimethyl-6-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate | C18H24O6S | 详情 | 详情 | |
| (XI) | 41915 | ((2R,3S,4R,5R)-4,5-bis(acetoxy)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]tetrahydro-2-furanyl)methyl benzoate | C19H24O8S | 详情 | 详情 | |
| (XII) | 41916 | [(2R,3S,4R,5R)-4-(acetoxy)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C22H26N2O8S | 详情 | 详情 | |
| (XIII) | 41917 | [(2R,3R,4R,5R)-4-hydroxy-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C20H24N2O7S | 详情 | 详情 | |
| (XIV) | 41918 | ((2R,3S,4R,5R)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3,4-bis[[(4-methylphenyl)sulfonyl]oxy]tetrahydro-2-furanyl)methyl benzoate | C31H30N2O11S2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The selective protection of 1,2-O-isopropylidene-D-xylofuranose (I) with Tbdms-Cl and pyridine gives the silyl ether (II), which is oxidized with CrO3, pyridine and Ac2O in dichloromethane to yield the ketone (III). Stereoselective addition of trimethylsilylacetylene (IV) to the ketone (III) by means of BuLi in THF affords the beta-adduct (V), which is desilylated by means of TBAF in THF to provide 3-C-ethynyl-2,3-o-isopropylidene-alpha-D-ribofuranose (VI). The selective monobenzoylation of (VI) with benzoyl chloride and pyridine gives the monobenzoate (VII), which is treated with HCl in methanol to cleave the isopropylidene protecting group and yield (VIII). The exhaustive benzoylation of (VIII) with benzoyl chloride and DMAP in pyridine at 100 C affords the tribenzoate (IX), which is treated with H2SO4 and Ac2O to provide the monoacetate (X). The condensation of (X) with cytosine (XI) by means of SnCl4 in acetonitrile gives the cytidine derivative (XII), which is finally debenzoylated by means of NH3 in methanol to yield the target ethynyl-cytidine derivative.
| 【1】 Nomura, M.; Sato, T.; Masato, W.; Tanaka, M.; Asao, T.; Shuto, S.; Matsuda, A.; Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbruggen glycosylation . Tetrahedron 2002, 58, 7, 1279. |
| 【3】 Hattori, H.; et al.; Nucleosides and nucleotides. 158. 1-(3-C-Ethynyl-beta-D-ribo-pentofuranosyl)cytosine, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil, and their nucleobase analogues as new potential multifunctional antitumor nucleosides with a broad spectrum of activity. J Med Chem 1996, 39, 25, 5005. |
| 【2】 Nozawa, E.; Hattori, H.; Shuto, S.; Tanaka, M.; Sasaki, T.; Matsuda, A.; Synthesis and antitumor activity of 1-(3-C-ethynyl-beta-D-ribo-pentfuranosyl)cytosine, -uracil and their sugar modified derivatives. Nucleic Acids Symp Ser 1996, 35, 31. |
| 【4】 Matsuda, A.; Sasaki, T. (Taiho Pharmaceutical Co., Ltd.); 3'-Substd. nucleoside derivs.. EP 0747389; WO 9618636 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 41907 | (3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | 20031-21-4 | C8H14O5 | 详情 | 详情 |
| (II) | 54394 | (3aR,5R,6S,6aR)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | C14H28O5Si | 详情 | 详情 | |
| (III) | 54395 | (3aR,5R,6aS)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyldihydrofuro[2,3-d][1,3]dioxol-6(5H)-one | C14H26O5Si | 详情 | 详情 | |
| (IV) | 23897 | ethynyl(trimethyl)silane；trimethylsilyl acetylene | 1066-54-2 | C5H10Si | 详情 | 详情 |
| (V) | 54396 | (3aR,5R,6R,6aR)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-6-[2-(trimethylsilyl)ethynyl]tetrahydrofuro[2,3-d][1,3]dioxol-6-ol | C19H36O5Si2 | 详情 | 详情 | |
| (VI) | 54397 | (3aR,5R,6R,6aR)-6-ethynyl-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | C10H14O5 | 详情 | 详情 | |
| (VII) | 54398 | [(3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate | C17H18O6 | 详情 | 详情 | |
| (VIII) | 54399 | [(2R,3S,4R,5S)-3-ethynyl-3,4-dihydroxy-5-methoxytetrahydro-2-furanyl]methyl benzoate | C15H16O6 | 详情 | 详情 | |
| (IX) | 54400 | [(2R,3R,4R,5S)-3,4-bis(benzoyloxy)-3-ethynyl-5-methoxytetrahydro-2-furanyl]methyl benzoate | C29H24O8 | 详情 | 详情 | |
| (X) | 54401 | [(2R,3R,4R,5R)-5-(acetyloxy)-3,4-bis(benzoyloxy)-3-ethynyltetrahydro-2-furanyl]methyl benzoate | C30H24O9 | 详情 | 详情 | |
| (XI) | 12706 | Cytosine; 4-Amino-2(1H)-pyrimidinone | 71-30-7 | C4H5N3O | 详情 | 详情 |
| (XII) | 54402 | [(2R,3R,4R,5R)-5-[4-amino-2-oxo-1(2H)-pyrimidinyl]-3,4-bis(benzoyloxy)-3-ethynyltetrahydro-2-furanyl]methyl benzoate | C32H25N3O8 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)The reaction of 1,2-O-isopropylidene-D-xylofuranose (I) with 4-chlorobenzoyl chloride (II) and TEA gives the 5-O-(4-chlorobenzoate) (III), which is oxidized with TEMPO and NaClO to yield the 3-oxo derivative (IV). The ethynylation of (IV) by means of trimethylsilylethynyl magnesium bromide (V) affords the 3-C-trimethylsilylethynyl derivative (VI), which is hydrolyzed by means of refluxing aqueous HCOOH to provide the 3-C-ethynylated sugar (VII). The acylation of (VII) by means of 4-chlorobenzoyl chloride (II), TEA and DMAP gives the tetrabenzoate sugar (VIII), which is used for the glycosylation of bis trimethylsilyl cytosine (IX) by means of SnCl4 to yield the protected precursor (X). Finally, this compound is desilylated and debenzoylated by means of DBU in hot methanol to afford the target nucleoside.
| 【1】 Nomura, M.; Sato, T.; Masato, W.; Tanaka, M.; Asao, T.; Shuto, S.; Matsuda, A.; Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbruggen glycosylation . Tetrahedron 2002, 58, 7, 1279. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 41907 | (3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | 20031-21-4 | C8H14O5 | 详情 | 详情 |
| (II) | 10295 | p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride | 122-01-0 | C7H4Cl2O | 详情 | 详情 |
| (III) | 61573 | [(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 4-chlorobenzoate | C15H17ClO6 | 详情 | 详情 | |
| (IV) | 61574 | [(3aR,5R,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 4-chlorobenzoate | C15H15ClO6 | 详情 | 详情 | |
| (V) | 34561 | methyl 3-methyl-1-(2-methylphenyl)-2-(trimethylsilyl)-1H-pyrrolo[3,2-c]quinolin-6-yl ether; 6-methoxy-3-methyl-1-(2-methylphenyl)-2-(trimethylsilyl)-1H-pyrrolo[3,2-c]quinoline | C23H26N2OSi | 详情 | 详情 | |
| (VI) | 61575 | {(3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-6-[2-(trimethylsilyl)ethynyl]tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}methyl 4-chlorobenzoate | C20H25ClO6Si | 详情 | 详情 | |
| (VII) | 61576 | {(2R,3S,4R)-3,4,5-trihydroxy-3-[2-(trimethylsilyl)ethynyl]tetrahydro-2-furanyl}methyl 4-chlorobenzoate | C17H21ClO6Si | 详情 | 详情 | |
| (VIII) | 61577 | (3R,4R,5R)-3,4-bis[(4-chlorobenzoyl)oxy]-5-{[(4-chlorobenzoyl)oxy]methyl}-4-[2-(trimethylsilyl)ethynyl]tetrahydro-2-furanyl 4-chlorobenzoate | C38H30Cl4O9Si | 详情 | 详情 | |
| (IX) | 61578 | N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-4-pyrimidinamine; N-(trimethylsilyl)-N-{2-[(trimethylsilyl)oxy]-4-pyrimidinyl}amine | C10H21N3OSi2 | 详情 | 详情 | |
| (X) | 61579 | (2R,3R,4R,5R)-4-[(4-chlorobenzoyl)oxy]-5-{[(4-chlorobenzoyl)oxy]methyl}-2-[2-oxo-4-[(trimethylsilyl)amino]-1(2H)-pyrimidinyl]-4-[2-(trimethylsilyl)ethynyl]tetrahydro-3-furanyl 4-chlorobenzoate | C38H38Cl3N3O8Si2 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)The acylation of 2,3-O-isopropylidene-alpha-D-xylofuranose (I) with benzoyl chloride and pyridine gives the dibenzoyl ester (II), which is deprotected by means of H2SO4/HOAc in hot THF to yield 3,5-di-O-benzoyl-alpha-D-xylofuranose (III). The reaction of (III) with PPh3, I2 and imidazole in dichloromethane affords the glycal (IV), which is used in the glycosylation of the N,O-disilylated 5-fluorocytosine (V) by means of NIS in dichloromethane to provide the 2'-alpha-iodonucleoside (VI). The treatment of (VI) with Zn in EtOH/ethyl acetate (HOAc is used as catalyst) gives the unsaturated nucleoside (VII), which is finally debenzoylated by means of butylamine in THF.
| 【1】 Chen, S.-H.; Lin, S.; King, I.; Spinka, T.; Dutschman, G.E.; Gullen, E.A.; Cheng, Y.-C.; Doyle, T.W.; Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C. Bioorg Med Chem Lett 1998, 8, 22, 3245. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 41907 | (3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | 20031-21-4 | C8H14O5 | 详情 | 详情 |
| (II) | 56701 | [(3aR,5R,6S,6aR)-6-(benzoyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate | C22H22O7 | 详情 | 详情 | |
| (III) | 56702 | [(2R,3R,4R,5S)-3-(benzoyloxy)-4,5-dihydroxytetrahydro-2-furanyl]methyl benzoate | C19H18O7 | 详情 | 详情 | |
| (IV) | 56703 | [(2R,3R)-3-(benzoyloxy)-2,3-dihydro-2-furanyl]methyl benzoate | C19H16O5 | 详情 | 详情 | |
| (V) | 36959 | 5-fluoro-N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-4-pyrimidinamine; N-[5-fluoro-2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-N-(trimethylsilyl)amine | C10H20FN3OSi2 | 详情 | 详情 | |
| (VI) | 56704 | [(2R,3S,4R,5R)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-3-(benzoyloxy)-4-iodotetrahydro-2-furanyl]methyl benzoate | C23H19FIN3O6 | 详情 | 详情 | |
| (VII) | 56705 | {(2S,5R)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl}methyl benzoate | C16H14FN3O4 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(XXIII)Reaction of L-xylose (XXII) with acetone and H2SO4 gives the acetonide (XXIII), which by acylation with benzoyl chloride in pyridine/chloroform yields the dibenzoate (XXIV). The hydrolysis of acetonide (XXIV) with acetic acid to the dihydroxy sugar (XXV) followed by acylation with acetic anhydride provides the tetracylated L-xylose (XXVI). Condensation of compound (XXVI) with 2,4-bis(trimethylsilyloxy)pyrimidine (XXVII) - obtained by silylation of uracil (XXVIII) with hexamethyldisilazane - by means of trimethylsilyl triflate in 1,2-dichloroethane affords nucleoside (XXIX). Selective hydrolysis of the acetate ester of compound (XXIX) using hydrazine and AcOH in pyridine yields the dibenzoylated xylofuranosyl-uracil (XXX). Isomerization of compound (XXX) to the arabinofuranosyl analogue (XXXI) is achieved by reaction with dicyclohexylcarbodiimide and dichloroacetic acid in DMSO/benzene, followed by treatment with NaBH4 in EtOH/benzene. Subsequent deoxygenation of the 2'-hy-droxyl group of compound (XXXI) to afford 2'-deoxynucleoside (XX) is effected via condensation with phenyl chlorothionoformate, and then reduction of the resulting thiocarbonate (XXXII) with tris(trimethylsilyl)silane and AIBN. Iodination of the uracil ring of (XX) with I2 and cerium ammonium nitrate (CAN) in acetonitrile produces the 5-iodo derivative (XXXIII), which is protected at the 3-nitrogen atom by condensation with p-toluoyl chloride to yield the protected nucleoside (XXXIV). Introduction of the 5-methyl group to give the thymidine derivative (XXXV) is then effected by reaction of the 5-iodouracil (XXXIV) with tetramethyltin in the presence of palladium catalyst. Finally, all protecting groups of compound (XXXV) are removed by treatment with methanolic ammonia.
| 【1】 Gosselin, G.; Bergogne, M.C.; Imbach, J.L.; Synthesis and antiviral evaluation of beta-L-xylo-furanosyl nucleosides of the five naturally occurring nucleic acid bases. J Heterocycl Chem 1993, 30, 5, 1229. |
| 【2】 Sorbera, L.A.; Castañer, J.; Castañer, R.M.; Bayes, M.; Telbivudine. Drugs Fut 2003, 28, 9, 870. |
| 【3】 Gosselin, G.; Imbach, J.-L.; Aubertin, A.-M.; Sommadossi, J.-P.; Schinazi, R.F. (CNRS (Centre National de la Recherche Scientifique)); 2' or 3'-Deoxy and 2'-dideoxy-beta-L-pentafuranonucleoside cpds., method of preparation and application in therapy, especially as anti-viral agents. DE 2709754; EP 0717748; WO 9507287 . |
| 【4】 Bryant, M.L.; Gosselin, G.; Imbach, J.-L. (CNRS (Centre National de la Recherche Scientifique); Novirio Pharmaceuticals Ltd.); beta-L-2'-Deoxy-nucleosides for the treatment of hepatitis B. WO 0009531 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XX) | 39996 | [(2S,3R,5S)-3-(benzoyloxy)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C23H20N2O7 | 详情 | 详情 | |
| (XXII) | 62919 | (3S,4S,5S)-5-(hydroxymethyl)tetrahydro-2,3,4-furantriol | C5H10O5 | 详情 | 详情 | |
| (XXIII) | 41907 | (3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol | 20031-21-4 | C8H14O5 | 详情 | 详情 |
| (XXIV) | 56701 | [(3aR,5R,6S,6aR)-6-(benzoyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate | C22H22O7 | 详情 | 详情 | |
| (XXV) | 56702 | [(2R,3R,4R,5S)-3-(benzoyloxy)-4,5-dihydroxytetrahydro-2-furanyl]methyl benzoate | C19H18O7 | 详情 | 详情 | |
| (XXVI) | 39991 | [(2S,3R,4S)-4,5-bis(acetoxy)-3-(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate | C23H22O9 | 详情 | 详情 | |
| (XXVII) | 29619 | 2,4-bis[(trimethylsilyl)oxy]pyrimidine; trimethylsilyl 2-[(trimethylsilyl)oxy]-4-pyrimidinyl ether | C10H20N2O2Si2 | 详情 | 详情 | |
| (XXVIII) | 30921 | 2,4(1H,3H)-pyrimidinedione; Uracil | 66-22-8 | C4H4N2O2 | 详情 | 详情 |
| (XXIX) | 39992 | (2S,3R,4S,5S)-4-(acetoxy)-2-[(benzoyloxy)methyl]-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl benzoate | C25H22N2O9 | 详情 | 详情 | |
| (XXX) | 39993 | [(2S,3S,4S,5S)-3-(benzoyloxy)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-4-hydroxytetrahydro-2-furanyl]methyl benzoate | C23H20N2O8 | 详情 | 详情 | |
| (XXXI) | 39994 | [(2S,3R,4R,5S)-3-(benzoyloxy)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-4-hydroxytetrahydro-2-furanyl]methyl benzoate | C23H20N2O8 | 详情 | 详情 | |
| (XXXII) | 39995 | [(2S,3S,4R,5S)-3-(benzoyloxy)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-4-[(phenoxycarbothioyl)oxy]tetrahydro-2-furanyl]methyl benzoate | C30H24N2O9S | 详情 | 详情 | |
| (XXXIII) | 40002 | [(2S,3R,5S)-3-(benzoyloxy)-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C23H19IN2O7 | 详情 | 详情 | |
| (XXXIV) | 40003 | [(2S,3R,5S)-3-(benzoyloxy)-5-[5-iodo-3-(4-methylbenzoyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C31H25IN2O8 | 详情 | 详情 | |
| (XXXV) | 40004 | [(2S,3R,5S)-3-(benzoyloxy)-5-[5-methyl-3-(4-methylbenzoyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C32H28N2O8 | 详情 | 详情 |