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【结 构 式】 
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【分子编号】12706 【品名】Cytosine; 4-Amino-2(1H)-pyrimidinone 【CA登记号】71-30-7 |
【 分 子 式 】C4H5N3O 【 分 子 量 】111.10332 【元素组成】C 43.24% H 4.54% N 37.82% O 14.4% |
合成路线1
该中间体在本合成路线中的序号：(XII)2) The reaction of 2(R),3-O-isopropylideneglycerol (IV) with benzyl bromide by means of benzyltriethylammonium bromide (BTA) in refluxing aqueous NaOH gives (S)-3-O-benzylglycerol (V), which is monotritylated with 4-methoxytriphenylmethyl chloride (VI) and dimethylaminopyridine (DMAP) yielding the secondary alcohol (VII). The condensation of (VII) with diethyl tosyloxymethylphosphonate (VIII) by means of NaH in THF affords the fully protected phosphorylmethoxy derivative (IX), which is detritylated by treatment with aqueous acetic acid at 100 C to give 3-benzyloxy-2(S)-(diethoxyphosphorylmethoxy)-1-propanol (X). The reaction of (X) with methanesulfonyl chloride and triethylamine in dichloromethane yields the corresponding mesylate (XI), which is condensed with cytosine (XII) by means of cesium carbonate in hot DMF affording 1-[3-benzyloxy-2(S)-(diethoxyphosphorylmethoxy)propyl]cytosine (XIII). The debenzylation of (XIII) by treatment with Pd(OH)2 on carbon in refluxing ethanol/cyclohexene gives the corresponding alcohol (XIV), which is finally treated with bromotrimethylsilane in acetonitrile to eliminate the ethyl groups of the phosphonate.
| 【1】 Martin, J.C.; Webb, R.R. II, Wos, J.A.; Bronson, J.J.; Synthesis of (S)-N1-(3-hydroxy-2-phosphonylmethoxy)propylcytosine, (S)-HPMPC. Tetrahedron Lett 1988, 29, 5475-8. |
| 【2】 Fromtling, R.A.; Castaner, J.; Cidofovir. Drugs Fut 1996, 21, 10, 1003. |
| 【3】 Bronson, J.J.; Ghazzouli, I.; Hitchcock, M.J.M.; Webb, R.R. II, Martin, J.C.; Synthesis and antiviral activity of the nucleotide analogue (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cytosine. J Med Chem 1989, 32, 7, 1457-63. |
| 【4】 Martin, J.C.; Bronson, J.J.; Webb, R.R. II, Hitchcock, M.J.M.; Ghazzouli, I.; Synthesis and antiherpesvirus activity of (S)-1-((3-hydroxy-2-phosphonylmethoxy)propyl)cytosine (HPMPC) and related nucleotide analogues. Nucleosides Nucleotides 1989, 8, 5-6, 923-6. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 12698 | [(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanol | 14347-78-5 | C6H12O3 | 详情 | 详情 |
| (V) | 12699 | (2S)-3-(Benzyloxy)-1,2-propanediol; (S)-(-)-1-Benzylglycerol | 17325-85-8 | C10H14O3 | 详情 | 详情 |
| (VI) | 12700 | 4-[Chloro(diphenyl)methyl]phenyl methyl ether; 1-[Chloro(diphenyl)methyl]-4-methoxybenzene; p-Anisylchlorodiphenylmethane | 14470-28-1 | C20H17ClO | 详情 | 详情 |
| (VII) | 12701 | (2R)-1-(Benzyloxy)-3-[(4-methoxyphenyl)(diphenyl)methoxy]-2-propanol | C30H30O4 | 详情 | 详情 | |
| (VIII) | 12702 | (diethoxyphosphoryl)methyl 4-methylbenzenesulfonate | 31618-90-3 | C12H19O6PS | 详情 | 详情 |
| (IX) | 12703 | diethyl [((1R)-2-(benzyloxy)-1-[[(4-methoxyphenyl)(diphenyl)methoxy]methyl]ethyl)oxy]methylphosphonate | C35H41O7P | 详情 | 详情 | |
| (X) | 12704 | diethyl [[(1S)-2-(benzyloxy)-1-(hydroxymethyl)ethyl]oxy]methylphosphonate | C15H25O6P | 详情 | 详情 | |
| (XI) | 12705 | (2R)-3-(benzyloxy)-2-[(diethoxyphosphoryl)methoxy]propyl methanesulfonate | C16H27O8PS | 详情 | 详情 | |
| (XII) | 12706 | Cytosine; 4-Amino-2(1H)-pyrimidinone | 71-30-7 | C4H5N3O | 详情 | 详情 |
| (XIII) | 12707 | diethyl ([(1S)-2-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1-[(benzyloxy)methyl]ethyl]oxy)methylphosphonate | C19H28N3O6P | 详情 | 详情 | |
| (XIV) | 12708 | diethyl [[(1S)-2-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethyl]oxy]methylphosphonate | C12H22N3O6P | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XII)3) The reaction of 2(S),3-O-isopropylideneglycerol (XV) with methanesulfonyl chloride and triethylamine in dichloromethane gives the corresponding mesylate (XVI), which is condensed with cytosine (XII) by means of cesium carbonate as before yielding 1-[2(S),3-(isopropylidenedioxy)propyl]cytosine (XVII). The deprotection of (XVII) with aqueous acetic acid at 100 C affords the corresponding diol (XVIII), which is treated with trityl chloride, DMAP and triethylamine in DMF to give the monotrityl compound (XIX). The condensation of (XIX) with diethyl tosyloxymethylphosphonate (VIII) [obtained by reaction of diethylphosphite (XX) with paraformaldehyde, followed by tosylation with tosyl chloride] by a previous treatment of (XX) with DMF dimethylacetal, then condensation by means of NaH in DMF, and a final hydrolysis with hot aqueous acetic acid yields the 1-[2(S)-(diethoxyphosphorylmethoxy)-3-hydroxypropyl]cytosine (XIV) (already obtained), which is finally treated with bromotrimethylsilane as before. 4) The reaction of the acetonide (XVI) with N4-benzoylcytosine (XXI) by means of potassium tert-butoxide or cesium carbonate gives the condensation product (XXII), which is deprotected with HCl in acetic acid yielding the diol (XXIII). The reaction of (XXIII) with trityl chloride and DMAP in refluxing pyridine affords the monotritylated compound (XXIV), which is condensed with the phosphonate (VIII) by means of NaH in DMF to give the fully protected HPMPC compound (XXV). The successive deprotections of (XXV), first with HCl in dichloromethane to eliminate the trityl group yielding (XXVI), then with bromotrimethylsilane to obtain the free phosphono group giving (XXVII), and finally with concentrated aqueous NH4OH to eliminate the benzoyl group affords cidofovir. 5) The benzoylation of acetonide derivative (XVII) with benzoyl anhydride in refluxing pyridine gives the benzoyl citosine derivative (XXII) already obtained.
| 【1】 Fromtling, R.A.; Castaner, J.; Cidofovir. Drugs Fut 1996, 21, 10, 1003. |
| 【2】 Bronson, J.J.; Ferrara, L.M.; Howell, H.G.; Brodfuehrer, P.R.; Martin, J.C.; A new synthesis of the potent and selective anti-herpesvirus agent (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cytosine. Nucleosides Nucleotides 1990, 9, 6, 745-69. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 12702 | (diethoxyphosphoryl)methyl 4-methylbenzenesulfonate | 31618-90-3 | C12H19O6PS | 详情 | 详情 |
| (XII) | 12706 | Cytosine; 4-Amino-2(1H)-pyrimidinone | 71-30-7 | C4H5N3O | 详情 | 详情 |
| (XIV) | 12708 | diethyl [[(1S)-2-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethyl]oxy]methylphosphonate | C12H22N3O6P | 详情 | 详情 | |
| (XV) | 12709 | [(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanol | 22323-82-6 | C6H12O3 | 详情 | 详情 |
| (XVI) | 12710 | [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate | C7H14O5S | 详情 | 详情 | |
| (XVII) | 12711 | 4-Amino-1-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2(1H)-pyrimidinone | C10H15N3O3 | 详情 | 详情 | |
| (XVIII) | 12695 | 4-Amino-1-[(2S)-2,3-dihydroxypropyl]-2(1H)-pyrimidinone | C7H11N3O3 | 详情 | 详情 | |
| (XIX) | 12713 | 4-Amino-1-[(2S)-2-hydroxy-3-(trityloxy)propyl]-2(1H)-pyrimidinone | C26H25N3O3 | 详情 | 详情 | |
| (XX) | 12714 | diethyl phosphonate; diethyl phosphite | 762-04-9 | C4H11O3P | 详情 | 详情 |
| (XXI) | 12715 | N-(2-Oxo-1,2-dihydro-4-pyrimidinyl)benzamide; N-Benzoylcytosine | 26661-13-2 | C11H9N3O2 | 详情 | 详情 |
| (XXII) | 12716 | N-(1-[[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl]-2-oxo-1,2-dihydro-4-pyrimidinyl)benzamide | C17H19N3O4 | 详情 | 详情 | |
| (XXIII) | 12717 | N-[1-[(2S)-2,3-Dihydroxypropyl]-2-oxo-1,2-dihydro-4-pyrimidinyl]benzamide | C14H15N3O4 | 详情 | 详情 | |
| (XXIV) | 12718 | N-[1-[(2S)-2-Hydroxy-3-(trityloxy)propyl]-2-oxo-1,2-dihydro-4-pyrimidinyl]benzamide | C33H29N3O4 | 详情 | 详情 | |
| (XXV) | 12719 | diethyl ([(1S)-2-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-1-[(trityloxy)methyl]ethyl]oxy)methylphosphonate | C38H40N3O7P | 详情 | 详情 | |
| (XXVI) | 12720 | diethyl [[(1S)-2-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethyl]oxy]methylphosphonate | C19H26N3O7P | 详情 | 详情 | |
| (XXVII) | 12721 | [[(1S)-2-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-1-(hydroxymethyl)ethyl]oxy]methylphosphonic acid | C15H18N3O7P | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(IV)There are two options for the synthesis of lamivudine: In the first approach the intact nucleoside analogue is prepared in racemic form by resolution to afford the required chiral product. This can be effected by an enzyme-mediated enantiospecific reaction. In the second approach synthesis of a chiral sugar component precedes coupling with the cytosine base under conditions where the chirality of the sugar precursor is maintained. The first approach is outlined in Scheme 18435601a. The oxathiolane (III) is obtained as a 1:1 mixture of anomers from reaction of benzoyloxyacetaldehyde (I) with mercaptoacetaldehyde dimethylacetal (II) in the presence of a Lewis acid. Treatment of (III) with silylated cytosine (IV) in the presence of TMS-triflate affords a 1:1 mixture of beta- and alpha-anomers (V) from which the required beta-anomer may be obtained by crystallization. Various alternative coupling conditions have been reported which yield almost exclusively the beta-anomer, notably as a result of the use of SnCl4. Subsequent deprotection affords the racemic nucleoside (VI) (BCH189). The resolution may be effected by a variety of enzymatic processes. Treatment of the nucleoside with phosphorus oxychloride and trimethylphosphate affords the 5'-monophosphate (VII). The natural enantiomer is selectively recognized by the 5'-nucleotidase from Crotalus atrox venom to afford the (+)-beta-D-nucleoside (VIII) and leave the unatural (-)-beta-L-enantiomer as the monophosphate (IX). Facile separation of these two products and subsequent dephosphorylation of (IX) using bacterial alkaline phosphatase affords lamivudine. Selective enzymatic recognition of the natural enantiomer may also be used to advantage in the resolution using cytidine deaminase derived from E. coli. In this case the enzyme is responsible for enantiospecific hydrolysis of the natural form to afford a readily separable mixture of lamivudine and the uridine derivative (X). Other enzymes including esterases and phosphodiesterases have application in the resolution of derivatives of the racemic nucleoside.
| 【1】 Choi, W.-B.; Yeola, S.; Liotta, D.C.; Wilson, L.S.; Schinazi, R.F.; In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of oxathiolanyl and dioxolanyl nucleoside analogues. J Am Chem Soc 1991, 113, 9377-9. |
| 【2】 Coates, J.A.V.; Mutton, I.M.; Penn, C.R.; Storer, R.; Williamson, C. (BioChem Pharma Inc.); 1,3-Oxathiolane nucleoside analogues. EP 0625150; JP 1993501117; JP 1999080153; JP 2000128787; WO 9117159 . |
| 【3】 Belleau, B.; Nguyen-Ba, N. (BioChem Pharma Inc.); Substd.-1,3-oxathiolanes with antiviral properties. EP 0382526; EP 0711771; JP 1996119967; JP 2000143662; US 5047407 . |
| 【4】 Storer, R.; Belleau, B.; Noble, S.A.; Lamont, B.; Clemens, I.R.; Williamson, C.; The resolution and absolute stereochemistry of the enantiomers of cis-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (BCH189): Equipotent anti-HIV agents. Nucleosides Nucleotides 1993, 12, 2, 225. |
| 【5】 Storer, R.; Wilcox, P.; Daniel, M.; Collis, P.; Cameron, J.M.; Lamivudine. Drugs Fut 1993, 18, 4, 319. |
| 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) | 15605 | 2-oxoethyl benzoate | C9H8O3 | 详情 | 详情 | |
| (II) | 15606 | 2,2-dimethoxy-1-ethanethiol; 2,2-dimethoxyethylhydrosulfide | C4H10O2S | 详情 | 详情 | |
| (III) | 15607 | (5-methoxy-1,3-oxathiolan-2-yl)methyl benzoate | C12H14O4S | 详情 | 详情 | |
| (IV) | 12706 | Cytosine; 4-Amino-2(1H)-pyrimidinone | 71-30-7 | C4H5N3O | 详情 | 详情 |
| (V) | 15609 | [5-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,3-oxathiolan-2-yl]methyl benzoate | C15H15N3O4S | 详情 | 详情 | |
| (VI) | 15610 | 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone | C8H11N3O3S | 详情 | 详情 | |
| (VII) | 15611 | [5-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,3-oxathiolan-2-yl]methyl dihydrogen phosphate | C8H12N3O6PS | 详情 | 详情 | |
| (VIII) | 15612 | 4-amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone | C8H11N3O3S | 详情 | 详情 | |
| (IX) | 15613 | [(2R,5S)-5-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,3-oxathiolan-2-yl]methyl dihydrogen phosphate | C8H12N3O6PS | 详情 | 详情 | |
| (X) | 15614 | 1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione | C8H10N2O4S | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(XI)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5
该中间体在本合成路线中的序号：(V)Displacement of the chlorine atom of (I) with potassium benzoate in boiling DMF afforded benzoate ester (II). The hydroxymethyl group of (II) was subsequently oxidized to carboxylic acid (III) employing pyridinium dichromate. Conversion of acid (III) to the corresponding mixed anhydride with ethyl chloroformate, followed by Baeyer-Villiger oxidation with m-chloroperbenzoic acid, gave rise to the m-chlorobenzoyloxy dioxolane (IV). This was then coupled to cytosine (V) following a previously reported procedure to produce adduct (VI) as a cis/trans mixture. After acetylation with Ac2O, the desired cis-isomer (VII) was isolated by flash chromatography. The title compound was finally obtained by basic hydrolysis (VII).
| 【1】 Belleau, B.; Dixit, D.; Nguyen-Ba, N. (Shire BioChem Inc.); 2-Substd.-4-substd.-1,3-dioxolanes, synthesis and use thereof. EP 0337713 . |
| 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) | 56692 | [(2S,4R)-2-(chloromethyl)-1,3-dioxolan-4-yl]methanol | C5H9ClO3 | 详情 | 详情 | |
| (II) | 56693 | [(2S,4R)-4-(hydroxymethyl)-1,3-dioxolan-2-yl]methyl benzoate | C12H14O5 | 详情 | 详情 | |
| (III) | 25844 | (2S,4S)-2-[(benzoyloxy)methyl]-1,3-dioxolane-4-carboxylic acid | C12H12O6 | 详情 | 详情 | |
| (IV) | 56694 | (2S)-2-[(benzoyloxy)methyl]-1,3-dioxolan-4-yl 3-chlorobenzoate | C18H15ClO6 | 详情 | 详情 | |
| (V) | 12706 | Cytosine; 4-Amino-2(1H)-pyrimidinone | 71-30-7 | C4H5N3O | 详情 | 详情 |
| (VI) | 56695 | {(2S)-4-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,3-dioxolan-2-yl}methyl benzoate | C15H15N3O5 | 详情 | 详情 | |
| (VII) | 56696 | {(2S,4S)-4-[4-(acetylamino)-2-oxo-1(2H)-pyrimidinyl]-1,3-dioxolan-2-yl}methyl benzoate | C17H17N3O6 | 详情 | 详情 |