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【结 构 式】

【分子编号】60114

【品名】6-(trimethylsilyl)-5-hexynoic acid

【CA登记号】

【 分 子 式 】C9H16O2Si

【 分 子 量 】184.31034

【元素组成】C 58.65% H 8.75% O 17.36% Si 15.24%

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:(XVII)

Chiral acetylenic ketone intermediate (XXIV): The oxidation of 6-(trimethylsilyl)-5-hexyn-1-ol (XVI) with PCC in DMF gives the carboxylic acid (XVII), which is condensed with the chiral auxiliary (XVIII) by means of Piv-Cl and TEA in THF to yield the acyloxazolidine (XIX). The diastereoselective methylation of (XIX) with Me-I and NaHMDS in THF affords the methylated compound (XX), which by reductive elimination of the chiral auxiliary with LiBH4 in ethyl ether provides the chiral alcohol (XXI). The oxidation of (XXI) with (COCl)2 and DMSO in dichloromethane leads to the aldehyde (XXII), which by a Grignard reaction with Me-MgBr in ethyl ether is converted into the secondary alcohol (XXIII). Finally, this compound is oxidized with (COCl)2 as before to yield the chiral acetylenic ketone intermediate (XXIV)

1 Duan, M.S.; Paquette, L.A.; Enantioselective total synthesis of the cyclophilin-binding immunosuppressive agent sanglifehrin A. Angew Chem. Int Ed 2001, 40, 19, 3632.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVI) 60113 6-(trimethylsilyl)-5-hexyn-1-ol C9H18OSi 详情 详情
(XVII) 60114 6-(trimethylsilyl)-5-hexynoic acid C9H16O2Si 详情 详情
(XVIII) 25351 (4R)-4-benzyl-1,3-oxazolidin-2-one; (R)-(+)-4-benzyl-2-oxazolidinone 102029-44-7 C10H11NO2 详情 详情
(XIX) 60115 (4S)-4-benzyl-3-[6-(trimethylsilyl)-5-hexynoyl]-1,3-oxazolidin-2-one C19H25NO3Si 详情 详情
(XX) 60116 (4S)-4-benzyl-3-[(2S)-2-methyl-6-(trimethylsilyl)-5-hexynoyl]-1,3-oxazolidin-2-one C20H27NO3Si 详情 详情
(XXI) 60117 (2S)-2-methyl-6-(trimethylsilyl)-5-hexyn-1-ol C10H20OSi 详情 详情
(XXII) 60118 (2S)-2-methyl-6-(trimethylsilyl)-5-hexynal C10H18OSi 详情 详情
(XXIII) 60119 (3S)-3-methyl-7-(trimethylsilyl)-6-heptyn-2-ol C11H22OSi 详情 详情
(XXIV) 60120 (3S)-3-methyl-7-(trimethylsilyl)-6-heptyn-2-one C11H20OSi 详情 详情
Extended Information