|
【结 构 式】 
|
【分子编号】12206 【品名】1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine 【CA登记号】1463-10-1 |
【 分 子 式 】C10H14N2O6 【 分 子 量 】258.23104 【元素组成】C 46.51% H 5.46% N 10.85% O 37.17% |
合成路线1
该中间体在本合成路线中的序号：(XI)4) Reaction of thymine (IX) with 1-O-acetyl-2,3,5-tri-O-benzoylribose (X) and hexamethyldisilazane, trimethylsilyl chloride and trifluoromethanesulfonic acid in acetonitrile, followed by cleavage of the protecting groups with sodium methoxide in methanol gives 5-methyluridine (XI). Compound (XI) is converted to (XII) by means of 2-acetoxyisobutyryl bromide in acetonitrile, subsequent reaction of (XII) with zinc-copper in dimethylformamide yields (XIII), which is finally deprotected with sodium methoxide in methanol. 5) 5-Methyluridine (XI) can also be converted to (XIV) by means of trimethylorthoacetate in acetic acid. Compound (XIV) is then treated with hydrobromic acid to give (XV), which is treated with zinc in acetonitrile and EDTA or is successively treated with acetic anhydride, zirconium oxide and tributylamine.
| 【1】 Ineyama, T.; Shiragami, H.; Izawa, K.; Uchida, Y.; Synthesis of 1-(2,3-dideoxy-beta-d-glycero-pent-2-enofuranosyl)thymine (d4T; stavudine) from 5-methyluridine. Nucleosides Nucleotides 1996, 15, 1-3, 47. |
| 【2】 Ebata, T.; Matsushita, H.; Mizutani, N.; Itoh, K. (Japan Tobacco Inc.); Process for producing 2',3'-dideoxy-2',3'-didehydronucleoside. WO 9202516 . |
| 【3】 Shiragami, H.; Uchida, Y.; Izawa, K. (Ajinomoto Co., Inc.); Nucleoside derivs. and production thereof. EP 0519464 . |
| 【4】 Tortolani, D.R.; Brodfuehrer, P.R.; Starrett, J.E. Jr.; Martin, J.C.; Howell, H.G.; Mansuri, M.M.; Wos, J.A.; Preparation of 1-(2,3-ideoxy-beta-d-glycero-pent-2-enofuranosyl)thymine (d4T) and 2',30-dideoxyadenosine (ddA): General methods for the synthesis of 2',3'-olefinic and 2',3'-dideoxy nucleoside analogues active against HIV. J Org Chem 1989, 54, 4780-5. |
| 【5】 Robinson, C.; Castaner, J.; Stavudine. Drugs Fut 1994, 19, 10, 925. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 12204 | 5-Methyl-2,4(1H,3H)-pyrimidinedione; Thymine | 65-71-4 | C5H6N2O2 | 详情 | 详情 |
| (X) | 12205 | (2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]tetrahydro-2-furanyl acetate | C28H30O6 | 详情 | 详情 | |
| (XI) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (XII) | 12207 | [(2R,3R,4R,5R)-3-(acetoxy)-4-bromo-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl 2-(acetoxy)-2-methylpropanoate | C18H23BrN2O9 | 详情 | 详情 | |
| (XIII) | 12208 | [(2S,5R)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl 2-(acetoxy)-2-methylpropanoate | C16H20N2O7 | 详情 | 详情 | |
| (XIV) | 12209 | 1-[(3aR,4R,6R,6aR)-6-(Hydroxymethyl)-2-methoxy-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C13H18N2O7 | 详情 | 详情 | |
| (XV) | 12210 | (2R,3R,4R,5R)-4-bromo-2-(hydroxymethyl)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl acetate | C12H15BrN2O6 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)The synthesis of [1'-14C]-labeled stavudine has been published: The reaction of labeled D-ribofuranose (I) first with methanol and acetyl chloride and then with benzoyl chloride gives 2,3,5-tri-O-benzoyl-1-O-methyl-D-ribofuranoside (II), which is acetylated with acetic anhydride and acetic acid to 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranoside (III). The condensation of (III) with thymine (IV) by means of hexamethyldisylazane (HMDS), trimethylsilyl chloride (TMS-Cl) and trifluoromethanesulfonic acid, followed by a basic hydrolysis with NaOMe affords 1-(beta-D-ribofuranosyl)thymine (V), which is treated with methanesulfonyl chloride in pyridine giving the trimesylate (VI). The reaction of (VI) with sodium benzoate in hot DMF yields the benzoylated internal ether (VII), which is treated with acetyl bromide in acetic acid/HBr affording 1-[2-bromo-2-deoxy-5-O-benzoyl-3-O-(methanesulfonyl)-beta-D-ribofuranos yl]thymine (VIII). The reaction of (VIII) with Zn in the same solvent as before gives 5'-O-benzoylstavudine (IX), which is finally debenzoylated with NaOCH3 in methanol.
| 【1】 Discordia, R.P.; Synthesis of 1'-[C-14]-Stavudine(R) (d4T). J Label Compd Radiopharm 1996, 38, 7, 613. |
| 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) | 10016 | D-Ribose; (3R,4S,5R)-5-(Hydroxymethyl)tetrahydro-2,3,4-furantriol; (2R,3R,4R)-2,3,4,5-Tetrahydroxypentanal | 50-69-1 | C5H10O5 | 详情 | 详情 |
| (I) | 45109 | (3R,4S,5R)-5-(hydroxymethyl)tetrahydro-2,3,4-furantriol | C5H10O5 | 详情 | 详情 | |
| (II) | 12247 | [(2R,3R,4R)-3,4-bis(benzoyloxy)-5-methoxytetrahydro-2-furanyl]methyl benzoate | C27H24O8 | 详情 | 详情 | |
| (II) | 45110 | [(2R,3R,4R)-3,4-bis(benzoyloxy)-5-methoxytetrahydro-2-furanyl]methyl benzoate | C27H24O8 | 详情 | 详情 | |
| (III) | 17523 | [(2S,3S,4S,5R)-5-(acetoxy)-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate | 6974-32-9 | C28H24O9 | 详情 | 详情 |
| (III) | 45111 | [(2R,3R,4R,5S)-5-(acetoxy)-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate | C28H24O9 | 详情 | 详情 | |
| (IV) | 12204 | 5-Methyl-2,4(1H,3H)-pyrimidinedione; Thymine | 65-71-4 | C5H6N2O2 | 详情 | 详情 |
| (V) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (V) | 45112 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C10H14N2O6 | 详情 | 详情 | |
| (VI) | 12251 | 1-[(2R,3R,4R,5R)-3,4-Bis[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C19H32N2O6S3 | 详情 | 详情 | |
| (VI) | 45113 | 1-[(2R,3R,4R,5R)-3,4-bis[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C19H32N2O6S3 | 详情 | 详情 | |
| (VII) | 12252 | ((2R,3R,3aS,9aR)-7-methyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-2-yl)methyl benzoate | C20H22N2O6S | 详情 | 详情 | |
| (VII) | 45114 | ((2R,3R,3aS,9aR)-7-methyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-2-yl)methyl benzoate | C20H22N2O6S | 详情 | 详情 | |
| (VIII) | 12253 | [(2R,3R,4R,5R)-4-bromo-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C20H23BrN2O6S | 详情 | 详情 | |
| (VIII) | 45115 | [(2R,3R,4R,5R)-4-bromo-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C20H23BrN2O6S | 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 | |
| (IX) | 45116 | [(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 |
合成路线3
该中间体在本合成路线中的序号：(I)An improved process for the preparation of high purity stavudine in a good yield was reported: The reaction of 5-methyluridine (I) with mesyl chloride and NMM in acetone, followed by a treatment with 6N NaOH gives the 2,2'-anhydro-5-methyluridine derivative (II), which is treated successively with potassium benzoate in DMF, HBr in acetic acid, and finally with Zn in DMF to yield 2',3'-anhydro-5'-O-benzoylthymidine (III). Finally, this compound is debenzoylated with hot butylamine.
| 【1】 Reddy, J.P.; Quinlan, S.L.; Reid, J.G.; Renner, D.A.; Weaver, D.G.; Stark, D.R.; Chen, B.-C.; Independent syntesis and fate studies of impurities in process intermediates of the anti-AIDS drug d4T. Org Process Res Dev 1998, 2, 3, 203. |
| 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) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (II) | 41035 | (2R,3R,3aS,9aR)-7-methyl-2-[[(methylsulfonyl)oxy]methyl]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-yl methanesulfonate | C12H16N2O9S2 | 详情 | 详情 | |
| (III) | 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 |
合成路线4
该中间体在本合成路线中的序号：(I)The sulfonation of 5-methyluridine (I) with MsCl and NMM in acetone gives the trimesylate (II) which is treated with sodium benzoate in hot acetamide to yield the cyclic benzoylated anhydro compound (III). The reaction of (III) with acetyl bromide in methanol/ethyl acetate affords the bromo derivative (IV), which is debrominated with Zn in the same solvent with a catalytic amount of HOAc to furnish the unsaturated sugar derivative (V). Finally this compound is debenzoylated with hot butylamine.
| 【1】 Chen, B.-C.; et al.; 5-Benzoyl-2'alpha-bromo-3'-O-methanesulfonylthymidine: A superior nucleoside for the synthesis of the anti-AIDS drug d4T(stavudine). Tetrahedron Lett 1995, 36, 44, 7957. |
| 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) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (II) | 12251 | 1-[(2R,3R,4R,5R)-3,4-Bis[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C19H32N2O6S3 | 详情 | 详情 | |
| (III) | 12252 | ((2R,3R,3aS,9aR)-7-methyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-2-yl)methyl benzoate | C20H22N2O6S | 详情 | 详情 | |
| (IV) | 12253 | [(2R,3R,4R,5R)-4-bromo-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C20H23BrN2O6S | 详情 | 详情 | |
| (V) | 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 |
合成路线5
该中间体在本合成路线中的序号：(I)The reaction of 5-methyluridine (I) with 1,1-dimethoxycyclopentane (II) by means of TsOH in hot dichloroethane gives the corresponding cyclic ketal (III), which is protected with 4-methoxybenzyl bromide and NaH in DME yielding the N,O-diprotected compound (IV). Elimination of the ketal protecting group of (IV) with dichloroacetic acid in water affords N3,O5'-bis(4-methoxybenzyl)-5-methyluridine (V), which is treated with PPh3, I2 and imidazole in hot toluene/acetonitrile to provide 2',3'-didehydro-2',3'-dideoxy-N3,O5’-bis(4-methoxybenzyl)-5-methyluridine (VI). Finally this compound is deprotected with ammonium cerium (IV) nitrate in acetonitrile/water.
| 【1】 Luzzio, F.A.; Menes, M.E.; A facile route to pyrimidine-based nuceloside olefins: Application to the synthesis of d4T(stavudine). J Org Chem 1994, 59, 24, 7267. |
| 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) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (II) | 41892 | 1,1-dimethoxycyclopentane; 1-methoxycyclopentyl methyl ether | 931-94-2 | C7H14O2 | 详情 | 详情 |
| (III) | 41893 | C15H20N2O6 | 详情 | 详情 | ||
| (IV) | 41894 | C31H36N2O7 | 详情 | 详情 | ||
| (V) | 41895 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(4-methoxyphenethyl)tetrahydro-2-furanyl]-3-(4-methoxybenzyl)-5-methyl-2,4(1H,3H)-pyrimidinedione | C26H30N2O7 | 详情 | 详情 | |
| (VI) | 41896 | 3-(4-methoxybenzyl)-1-[(2R,5R)-5-(4-methoxyphenethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C26H28N2O5 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(I)The reaction of 5-methyluridine (I) with TrCl and pyridine gives the 5'-O-trityl derivative (II), which is oxidized with NaIO4 in ethanol/water to yield the dialdehyde (III). The Wittig reaction of (III) with methyltriphenylphosphonium bromide (IV) and t-BuOK in toluene to afford the bis vinyl compound (V), which is submitted to a ring closing metathesis reaction catalyzed by a Ru catalyst in dichloromethane to provide the unsaturated nucleoside (VI). Finally, this compound is deprotected by means of AcOH in water to furnish the target Stavudine.
| 【1】 Ewing, D.F.; et al.; Synthesis of acyclic bis-vinyl pyrimidines: A general route to d4T via metathesis. Tetrahedron 2003, 59, 7, 941. |
| 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) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (II) | 41905 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(trityloxy)methyl]tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C29H28N2O6 | 详情 | 详情 | |
| (III) | 62190 | (2R)-2-({(1R)-1-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2-oxoethyl}oxy)-3-(trityloxy)propanal | C29H26N2O6 | 详情 | 详情 | |
| (IV) | 30484 | Methyl(triphenyl)phosphonium bromide | 1779-49-3 | C19H18BrP | 详情 | 详情 |
| (V) | 62191 | 5-methyl-1-[(1R)-1-({(1S)-1-[(trityloxy)methyl]-2-propenyl}oxy)-2-propenyl]-2,4(1H,3H)-pyrimidinedione | C31H30N2O4 | 详情 | 详情 | |
| (VI) | 12199 | 5-Methyl-1-[(2R,5S)-5-[(trityloxy)methyl]-2,5-dihydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | C29H26N2O4 | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(I)The reaction of 5-methyluridine (I) with trityl chloride (II) and pyridine gives the 5'-O-trityl analogue (III), which is submitted to an oxidative cleavage of the vicinal dihydroxy group by means of NaIO4 in EtOH/water to yield the dialdehyde (IV). The double Wittig olefination of (IV) by means of methyltriphenylphosphonium bromide (V) and t-BuOK in toluene affords the bis alkene (VI), which is submitted to a ring closing metathesis by means of the Grubb's catalyst in dichloromethane to provide the unsaturated nucleoside (VII). Finally, this compound was deprotected by means of 80% AcOH to furnish the target Stavudine.
| 【1】 Ewing, D.; Glacon, V.; Mackenzie, G.; Postel, D.; Len, C.; A novel approach to unsaturated acyclic nucleoside analogues and the first synthesis of d4T by ring closure metathesis. Tetrahedron Lett 2002, 43, 19, 3503. |
| 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) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (II) | 28630 | Triphenylchloromethane; 1-[Chloro(diphenyl)methyl]benzene; Trityl chloride | 76-83-5 | C19H15Cl | 详情 | 详情 |
| (III) | 41905 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(trityloxy)methyl]tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C29H28N2O6 | 详情 | 详情 | |
| (IV) | 62190 | (2R)-2-({(1R)-1-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2-oxoethyl}oxy)-3-(trityloxy)propanal | C29H26N2O6 | 详情 | 详情 | |
| (V) | 30484 | Methyl(triphenyl)phosphonium bromide | 1779-49-3 | C19H18BrP | 详情 | 详情 |
| (VI) | 62191 | 5-methyl-1-[(1R)-1-({(1S)-1-[(trityloxy)methyl]-2-propenyl}oxy)-2-propenyl]-2,4(1H,3H)-pyrimidinedione | C31H30N2O4 | 详情 | 详情 | |
| (VII) | 12199 | 5-Methyl-1-[(2R,5S)-5-[(trityloxy)methyl]-2,5-dihydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | C29H26N2O4 | 详情 | 详情 |
合成路线8
该中间体在本合成路线中的序号：(XXXVI)Condensation of 1-(b-L-ribofuranosyl)thymine (XXXVI) with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (XXXVII) in pyridine gives the cyclic disiloxane nucleoside (XXXVIII), which is acylated with thiocarbonyldiimidazole (TCDI) in DMF to yield the 2'-O-thioester derivative (XXXIX). Reduction of this compound by means of 2,2'-azobis(methylpropionitrile) (ABMP) and Bu3SnH in refluxing toluene affords the silylated 2'-deoxynucleoside (XL), which is finally desilylated by means of TBAF in THF.
| 【1】 Sorbera, L.A.; Castañer, J.; Castañer, R.M.; Bayes, M.; Telbivudine. Drugs Fut 2003, 28, 9, 870. |
| 【2】 Dowle, M.D.; Wu, W.-Y.; Jin, B.; Mason, A.M.; McConnell, D.; MacDonald, S.J.F.; Shanahan, S.E.; Nguyen, V.T.T. (Biota Scientific Management Pty Ltd.); Dimeric cpds. and their use as anti-viral agents. WO 0340135 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXXVI) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (XXXVII) | 29242 | 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane | 69304-37-6 | C12H28Cl2OSi2 | 详情 | 详情 |
| (XXXVIII) | 62920 | 1-[(6aS,8S,9S,9aR)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C22H40N2O7Si2 | 详情 | 详情 | |
| (XXXIX) | 62921 | O-{(6aS,8S,9S,9aS)-2,2,4,4-tetraisopropyl-8-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl} 1H-imidazole-1-carbothioate | C26H42N4O7SSi2 | 详情 | 详情 | |
| (XL) | 62922 | 1-[(6aS,8S,9aR)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C22H40N2O6Si2 | 详情 | 详情 |