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【结 构 式】

【分子编号】52187

【品名】(1S,2R,3R,4S,6Z,8S,9S,10S,11Z,13S,16R,17S,18R)-3,9,17-tris{[tert-butyl(dimethyl)silyl]oxy}-13-hydroxy-19-(methoxyamino)-2,4,6,8,10,16,18-heptamethyl-1-[(1S,2Z)-1-methyl-2,4-pentadienyl]-15,19-dioxo-6,11-nonadecadienyl carbamate

【CA登记号】

【 分 子 式 】C52H100N2O9Si3

【 分 子 量 】981.63058

【元素组成】C 63.63% H 10.27% N 2.85% O 14.67% Si 8.58%

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)

The Grignard reaction of the chiral pentanamide (I) with methylmagnesium bromide in ether gives the hydroxyhexanamide (II), which is oxidized with SO3/pyridine in DMSO to yield the oxohexanamide (III). The aldol condensation of the oxohexanamide (III) with the chiral aldehyde (IV) by means of (+)-beta-chlorodiisopinocampheylborane and TEA in ethyl ether affords the aldol (V), which is reduced with tetramethylammonium triacetoxyborohydride in acetonitrile/acetic acid to provide the dihydroxyamide (VI). Finally, this compound is deprotected and lactonized by treatment with HCl in THF/water to furnish the target discodermolide.

1 Kinder, F.R. (Novartis AG; Novartis-Erfindungen VmbH); Process for preparing discodermolide and analogues thereof. WO 0212220 .
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) 52184 (2R,3S,4R)-3-{[tert-Butyl(dimethyl)silyl]oxy}-N-methoxy-2,4-dimethyl-5-oxopentanamide C14H29NO4Si 详情 详情
(II) 52185 (2R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-N-methoxy-2,4-dimethylhexanamide C15H33NO4Si 详情 详情
(III) 52186 (2R,3S,4R)-3-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-2,4-dimethyl-5-oxohexanamide C15H31NO4Si 详情 详情
(IV) 42650 (1S,2R,3R,4S,6Z,8S,9S,10S,11Z)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-2,4,6,8,10-pentamethyl-1-[(1S,2Z)-1-methyl-2,4-pentadienyl]-13-oxo-6,11-tridecadienyl carbamate C37H69NO5Si2 详情 详情
(V) 52187 (1S,2R,3R,4S,6Z,8S,9S,10S,11Z,13S,16R,17S,18R)-3,9,17-tris{[tert-butyl(dimethyl)silyl]oxy}-13-hydroxy-19-(methoxyamino)-2,4,6,8,10,16,18-heptamethyl-1-[(1S,2Z)-1-methyl-2,4-pentadienyl]-15,19-dioxo-6,11-nonadecadienyl carbamate C52H100N2O9Si3 详情 详情
(VI) 52188 (1S,2R,3R,4S,6Z,8S,9S,10S,11Z,13S,15S,16S,17S,18R)-3,9,17-tris{[tert-butyl(dimethyl)silyl]oxy}-13,15-dihydroxy-19-(methoxyamino)-2,4,6,8,10,16,18-heptamethyl-1-[(1S,2Z)-1-methyl-2,4-pentadienyl]-19-oxo-6,11-nonadecadienyl carbamate C52H102N2O9Si3 详情 详情
Extended Information