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【结 构 式】

【分子编号】55076

【品名】1,3-oxathiolan-2-ylmethyl benzoate

【CA登记号】

【 分 子 式 】C11H12O3S

【 分 子 量 】224.28048

【元素组成】C 58.91% H 5.39% O 21.4% S 14.3%

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:(XII)

A new asymmetric synthesis has been reported. Oxidative cleavage of mono-benzoyl glycerol (IX) by means of NaIO4 provided aldehyde (X). Condensation of (X) with mercaptoethanol (XI) in the presence of ploystyryl diphenylphosphane-iodine complex gave rise to the oxathiolane (XII). Sharpless asymmetric oxidation of (XII) using tert-butyl hydroperoxide and L-diethyl tartrate led to an 82:18 mixture of (E)- and (Z)-sulfoxides (XIII) and (XIV). The desired (E)-isomer (XIII) was then isolated by column chromatography, displaying an enantiomeric excess of 60%. Coupling of (XIII) with N-acetylcytosine (VII) under Pummerer rearrangement conditions led to an equimolecular mixture of (Z)- and (E)-adducts (XV) and (XVI). After chromatographic separation of the desired (Z)-isomer (XV), the acetyl and benzoyl protecting groups were removed by treatment with sodium methoxide.

1 Caputo, R.; et al.; A new strategy for the asymmetric synthesis of 1,3-oxathiolane-based nucleoside analogues. Eur J Org Chem 1999, 6, 1455.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 55073 N(4)-Acetylcytosine 14631-20-0 C6H7N3O2 详情 详情
(IX) 55075 2,3-dihydroxypropyl benzoate C10H12O4 详情 详情
(X) 15605 2-oxoethyl benzoate C9H8O3 详情 详情
(XII) 55076 1,3-oxathiolan-2-ylmethyl benzoate C11H12O3S 详情 详情
(XIII) 55077 [(2R)-3-oxo-1,3lambda~4~-oxathiolan-2-yl]methyl benzoate C11H12O4S 详情 详情
(XIV) 55080 [(2S)-3-oxo-1,3lambda~4~-oxathiolan-2-yl]methyl benzoate C11H12O4S 详情 详情
(XV) 55078 {(2R,4R)-4-[4-(acetylamino)-2-oxo-1(2H)-pyrimidinyl]-1,3-oxathiolan-2-yl}methyl benzoate C17H17N3O5S 详情 详情
(XVI) 55079 {(2R,4S)-4-[4-(acetylamino)-2-oxo-1(2H)-pyrimidinyl]-1,3-oxathiolan-2-yl}methyl benzoate C17H17N3O5S 详情 详情
(XXI) 36375 2-Sulfanyl-1-ethanol; 2-Mercaptoethanol 60-24-2 C2H6OS 详情 详情
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