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

【结 构 式】

【分子编号】25269

【品名】(1R,2S)-3-(benzyloxy)-1-[(benzyloxy)methyl]-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)propyl methanesulfonate

【CA登记号】

【 分 子 式 】C26H40O6SSi

【 分 子 量 】508.7515

【元素组成】C 61.38% H 7.92% O 18.87% S 6.3% Si 5.52%

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:(V)

Opening of the (S,S)-epoxide (I) with the silylmethyl Grignard reagent (II) in the presence of CuI, followed by oxidative cleavage of the silyl alcohol (III) with H2O2 gave diol (IV). Then, selective protection of the primary hydroxyl group of (IV) with tert-butyldimethylsilyl chloride, followed by condensation with methanesulfonyl chloride, afforded mesylate (V). Subsequent alkylation of the sodium salt of ethyl mercaptoacetate (VI) gave thioether (VII). Desilylation of (VII) with tetrabutylammonium fluoride, followed by mesylation provided sulfonate (VIII). Subsequent intramolecular ring closure of (VIII) using NaH in DMF produced the tetrahydrothiophene (IX) as a 2:3 mixture of stereoisomers. Hydrolysis of the ethyl ester of (IX) with LiOH gave carboxylic acid (X), which was submitted to a modified Hunsdiecker reaction with Pb(OAc)4 to furnish the 1-O-acetate (XI) as a 1:1 anomeric mixture.

1 Upcroft, P.; Campbell, R.W.; Benakli, K.; Upcroft, J.A.; Vanelle, P.; Efficacy of new 5-nitroimidazoles against metronidazole-susceptible and -resistant Giardia, Trichomonas, and Entamoeba spp. Antimicrob Agents Chemother 1999, 43, 1, 73.
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) 25266 benzyl [(2S,3S)-3-[(benzyloxy)methyl]oxiranyl]methyl ether; (2S,3S)-2,3-bis[(benzyloxy)methyl]oxirane C18H20O3 详情 详情
(III) 25267 (2R,3R)-1,4-bis(benzyloxy)-3-[[isopropoxy(dimethyl)silyl]methyl]-2-butanol C24H36O4Si 详情 详情
(IV) 25268 (2R,3R)-4-(benzyloxy)-2-[(benzyloxy)methyl]-1,3-butanediol C19H24O4 详情 详情
(V) 25269 (1R,2S)-3-(benzyloxy)-1-[(benzyloxy)methyl]-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)propyl methanesulfonate C26H40O6SSi 详情 详情
(VI) 23995 ethyl 2-sulfanylacetate 2713-34-0 C4H8O2S 详情 详情
(VII) 25270 ethyl 2-[[(1S,2S)-3-(benzyloxy)-1-[(benzyloxy)methyl]-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)propyl]sulfanyl]acetate C29H44O5SSi 详情 详情
(VIII) 25271 ethyl 2-[((1S,2S)-3-(benzyloxy)-1-[(benzyloxy)methyl]-2-[[(methylsulfonyl)oxy]methyl]propyl)sulfanyl]acetate C24H32O7S2 详情 详情
(IX) 25272 ethyl (4R,5S)-4,5-bis[(benzyloxy)methyl]tetrahydro-2-thiophenecarboxylate C23H28O4S 详情 详情
(X) 25273 (4R,5S)-4,5-bis[(benzyloxy)methyl]tetrahydro-2-thiophenecarboxylic acid C21H24O4S 详情 详情
(XI) 25274 (4R,5S)-4,5-bis[(benzyloxy)methyl]tetrahydro-2-thiophenyl acetate C22H26O4S 详情 详情
Extended Information