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【结 构 式】 
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【分子编号】41898 【品名】(2R,3S)-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5-methoxytetrahydro-3-furanol 【CA登记号】 |
【 分 子 式 】C22H30O4Si 【 分 子 量 】386.5633 【元素组成】C 68.36% H 7.82% O 16.56% Si 7.27% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of 2-deoxy-D-ribose (I) with MeOH and HCl gives the methylglycoside (II), which is selectively silylated with TBDPSCl and DMAP in pyridine to yield the monosilylated glycoside (III). The reaction of (III) with TsCl in pyridine affords the 3'-tosylate (IV), which is condensed with the bis(trimethylsilyl)thymine (VI) by means of TMS-OTf in MeCN to provide 5'-O-(tert-butydiphenylsilyl)-3'-O-tosylthymidine (VII). Finally this compound is treated with TBAF in refluxing THF.
| 【1】 Kofoed, T.; Larsen, E.; Pedersen, E.B.; Synthesis of 2',3'-anhydro-2'-deoxyuridines and 2',3'-didehydro-2',3'-dideoxyuridines using polymer supported fluoride. Synthesis 1995, 1121. |
| 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) | 41897 | (4S,5R)tetrahydro-2H-pyran-2,4,5-triol | 35536-75-5 | C5H10O4 | 详情 | 详情 |
| (II) | 12241 | (2R,3S)-2-(Hydroxymethyl)-5-methoxytetrahydro-3-furanol | C6H12O4 | 详情 | 详情 | |
| (III) | 41898 | (2R,3S)-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5-methoxytetrahydro-3-furanol | C22H30O4Si | 详情 | 详情 | |
| (IV) | 41899 | (2R,3S)-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5-methoxytetrahydro-3-furanyl 4-methylbenzenesulfonate | C29H36O6SSi | 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) | 41901 | (2R,3S,5R)-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl 4-methylbenzenesulfonate | C33H38N2O7SSi | 详情 | 详情 |
Extended Information