• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】55199

【品名】tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(tritylsulfanyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

【CA登记号】

【 分 子 式 】C35H42N2O4S

【 分 子 量 】586.79556

【元素组成】C 71.64% H 7.21% N 4.77% O 10.91% S 5.46%

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:(LVI)

In a related procedure, aldehyde (XLVI) was condensed with triphenylmethanesulfenamide (LIV), producing the S-trityl sulfenimine (LV). Aldol-type condensation of (LV) with the silyloxy pyrrole (XLIX) gave rise to a diastereoisomeric mixture of adducts from which the desired isomer (LVI) was isolated as the major compound. Diastereoselectivity was increased using triflic acid as the condensation catalyst. Conjugate addition to (LVI) of propenylmagnesium bromide in the presence of CuBr yielded (LVII). Conversion of pyrrolidinone (LVII) to the cyano pyrrolidine (LVIII) was accomplished by the same sequence as above. Then, acidic cleavage of the tritylsulfanyl group of (LVIII), followed by N-acetylation, furnished the intermediate (XXXVII), which was finally processed as in the preceding methods.

1 Barnes, D.M.; et al.; Synthesis of an influenza neuraminidase inhibitor intermediate via a highly diastereoselective coupling reaction. Org Lett 2002, 4, 9, 1427.
2 Inhibitors of neuraminidases. WO 0128996 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXXVII) 55180 tert-butyl (2R,3S,5R)-2-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C22H37N3O4 详情 详情
(XLVI) 55189 (2S)-2-methoxy-2-methylpentanal C7H14O2 详情 详情
(XLIX) 55192 tert-butyl 2-{[tert-butyl(dimethyl)silyl]oxy}-1H-pyrrole-1-carboxylate C15H27NO3Si 详情 详情
(LIV) 55197 Triphenylmethanesulfenamide C19H17NS 详情 详情
(LV) 55198 N-[(E,2S)-2-methoxy-2-methylpentylidene](triphenyl)methanesulfenamide C26H29NOS 详情 详情
(LVI) 55199 tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(tritylsulfanyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate C35H42N2O4S 详情 详情
(LVII) 55200 tert-butyl (2R,3S)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(tritylsulfanyl)amino]pentyl}-5-oxo-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C38H48N2O4S 详情 详情
(LVIII) 55201 tert-butyl (2R,3S,5R)-5-cyano-2-{(1R,2S)-2-methoxy-2-methyl-1-[(tritylsulfanyl)amino]pentyl}-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C39H49N3O3S 详情 详情
Extended Information