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【结 构 式】

【分子编号】49209

【品名】N-(trimethylsilyl)-N-[7-(trimethylsilyl)-7H-purin-6-yl]benzamide

【CA登记号】

【 分 子 式 】C18H25N5OSi2

【 分 子 量 】383.6006

【元素组成】C 56.36% H 6.57% N 18.26% O 4.17% Si 14.64%

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:(X)

The enantioselective epoxidation of allyl alcohol (I) with 2-phenylisopropyl hydroperoxide (II) and Ti(iPrO)4 in the presence of D-diisopropyl tartrate gives the chiral epoxide (III), which is esterified with pivaloyl chloride to yield the pivalate (IV). The opening of the epoxide ring of (IV) by means of lithium acetylide (V) and BF3/Et2O affords the alkynyl alcohol (VI), which is cyclized by means of Mo(CO)6 and trimethylamine oxide to provide the chiral dihydrofuran (VII). The oxidation of (VII) with OsO4 and 4-methylmorpholine-N-oxide (NMMO) gives the diol (VIII), which is treated with Ac2O to yield the diacetate (IX). The condensation of (IX) with N6-benzoyl-N6,7-bis(trimethylsilyl)adenine (X) by means of Tms-OTf affords the nucleoside (XI). Finally, this compound is deprotected by means of NaOMe in methanol.

1 Gleason, M.M.; McDonald, F.E.; Asymmetric synthesis of nucleosides via molybdenum-catalyzed alkynol cycloisomerization coupled with stereoselective glycosylations of deoxyfuranose glycals and 3-amidofuranose glycals. J Am Chem Soc 1996, 118, 28, 6648.
2 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
(I) 12234 2-Propen-1-ol; Allyl alcohol 107-18-6 C3H6O 详情 详情
(II) 49206 alpha,alpha-Dimethylbenzyl hydroperoxide; Cumyl hydroperoxide; Cumene Hydroperoxide 80-15-9 C9H12O2 详情 详情
(III) 16260 (R)-(+)-Glycidol; (2R)-Oxiranemethanol; (2R)oxiranylmethanol 57044-25-4 C3H6O2 详情 详情
(IV) 12235 (2S)oxiranylmethyl pivalate C8H14O3 详情 详情
(V) 17461 ethynyllithium C2HLi 详情 详情
(VI) 12260 diethyl 2-(2,4,5-trifluoro-3-methoxybenzoyl)malonate C15H15F3O6 详情 详情
(VII) 12226 (2S)-2,3-dihydro-2-furanylmethyl pivalate C10H16O3 详情 详情
(VIII) 49207 [(2S,4R,5R)-4,5-dihydroxytetrahydro-2-furanyl]methyl pivalate C10H18O5 详情 详情
(IX) 49208 [(2S,4R,5S)-4,5-bis(acetoxy)tetrahydro-2-furanyl]methyl pivalate C14H22O7 详情 详情
(X) 49209 N-(trimethylsilyl)-N-[7-(trimethylsilyl)-7H-purin-6-yl]benzamide C18H25N5OSi2 详情 详情
(XI) 49210 [(2S,4R,5R)-4-(acetoxy)-5-[6-(benzoylamino)-9H-purin-9-yl]tetrahydro-2-furanyl]methyl pivalate C24H27N5O6 详情 详情
Extended Information