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【结 构 式】

【分子编号】12239

【品名】[(2S,4R,5R)-4-iodo-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl pivalate

【CA登记号】

【 分 子 式 】C15H21IN2O5

【 分 子 量 】436.24669

【元素组成】C 41.3% H 4.85% I 29.09% N 6.42% O 18.34%

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:(VI)

A new asymmetric synthesis of stavudine has been described: The regioselective epoxidation of allyl alcohol (I) by means of titanium tetraisopropoxide and alpha,alpha-dimethylbenzylperoxide, catalyzed by diisopropyl D-tartrate, followed by esterification with pivaloyl chloride yields the epoxide (II), which is then condensed with lithium acetylide catalyzed by boron trifluoride ethearate in THF, yielding the acetylenic alcohol (III). The cyclization of (III) catalyzed by Mo(CO)6 and trimethylamine oxide affords the dihydrofuran (IV), which is condensed with N,N'-bis(trimethylsilyl)thymine (V) and I2 to give the iodonucleoside (VI). Finally, this compound is dehydroiodinated and deprotected with sodium methoxide in methanol.

1 Gleason, M.M.; McDonald, F.E.; Asymmetric syntheses of stavudine (d4T) and cordycepin by cycloisomerization of alkynyl alcohols to endocyclic enol ethers. Angew Chem. Int Ed Engl 1995, 34, 3, 350.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
17461 ethynyllithium C2HLi 详情 详情
(I) 12234 2-Propen-1-ol; Allyl alcohol 107-18-6 C3H6O 详情 详情
(II) 12235 (2S)oxiranylmethyl pivalate C8H14O3 详情 详情
(III) 12236 (2S)-2-hydroxy-4-pentynyl pivalate C10H16O3 详情 详情
(IV) 12226 (2S)-2,3-dihydro-2-furanylmethyl pivalate C10H16O3 详情 详情
(V) 12238 5-Methyl-1,3-bis(trimethylsilyl)-2,4(1H,3H)-pyrimidinedione 3444-09-5 C11H22N2O2Si2 详情 详情
(VI) 12239 [(2S,4R,5R)-4-iodo-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl pivalate C15H21IN2O5 详情 详情
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