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【结 构 式】

【分子编号】55274

【品名】{(1R,2S,6R,10S,11R,13S,15R,17R)-13-benzyl-15-isopropenyl-4,17-dimethyl-5,6-bis[(trimethylsilyl)oxy]-12,14,18-trioxapentacyclo[11.4.1.0~1,10~.0~2,6~.0~11,15~]octadeca-4,8-dien-8-yl}methyl benzoate

【CA登记号】

【 分 子 式 】C41H54O7Si2

【 分 子 量 】715.04656

【元素组成】C 68.87% H 7.61% O 15.66% Si 7.86%

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:(XL)

Bromination at the alpha-position of ketone (XXXIX) to (XLI) was effected via formation of the corresponding silyl enol ether (XL), followed by treatment with N-bromosuccinimide. Dehydrohalogenation of the resultant bromo ketone (XLI) by means of lithium carbonate and lithium bromide in hot DMF afforded enone (XLII). Sequential removal of the O-silyl and benzoate protecting groups of (XLII) provided diol (XLIII). The C20 alcohol of (XLIII) was then esterified with the mixed anhydride (XLIV) to furnish the (4-O-acetyl)homovanillic ester (XLV). Finally, a soultion of pyrrolidine in CH2Cl2 was employed for the cleavage of the O-acetyl protecting group of (XLV).

1 Boger, D.L.; Searcey, M.; The first synthesis of a daphnane diterpene: The enantiocontrolled total synthesis of (+)-resiniferatoxin. Chemtracts - Org Chem 1998, 11, 9, 647.
2 Wender, P.A.; et al.; The first synthesis of a daphnane diterpene: The enantiocontrolled total synthesis of resiniferatoxin. J Am Chem Soc 1997, 119, 52, 12976.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXXIX) 55273 {(1R,2S,4S,6R,10S,11R,13S,15R,17R)-13-benzyl-15-isopropenyl-4,17-dimethyl-5-oxo-6-[(trimethylsilyl)oxy]-12,14,18-trioxapentacyclo[11.4.1.0~1,10~.0~2,6~.0~11,15~]octadec-8-en-8-yl}methyl benzoate C38H46O7Si 详情 详情
(XL) 55274 {(1R,2S,6R,10S,11R,13S,15R,17R)-13-benzyl-15-isopropenyl-4,17-dimethyl-5,6-bis[(trimethylsilyl)oxy]-12,14,18-trioxapentacyclo[11.4.1.0~1,10~.0~2,6~.0~11,15~]octadeca-4,8-dien-8-yl}methyl benzoate C41H54O7Si2 详情 详情
(XLI) 55275 {(1R,2S,6R,10S,11R,13S,15R,17R)-13-benzyl-4-bromo-15-isopropenyl-4,17-dimethyl-5-oxo-6-[(trimethylsilyl)oxy]-12,14,18-trioxapentacyclo[11.4.1.0~1,10~.0~2,6~.0~11,15~]octadec-8-en-8-yl}methyl benzoate C38H45BrO7Si 详情 详情
(XLII) 55276 {(1R,2S,6R,10S,11R,13S,15R,17R)-13-benzyl-15-isopropenyl-4,17-dimethyl-5-oxo-6-[(trimethylsilyl)oxy]-12,14,18-trioxapentacyclo[11.4.1.0~1,10~.0~2,6~.0~11,15~]octadeca-3,8-dien-8-yl}methyl benzoate C38H44O7Si 详情 详情
(XLIII) 55277 (1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-8-(hydroxymethyl)-15-isopropenyl-4,17-dimethyl-12,14,18-trioxapentacyclo[11.4.1.0~1,10~.0~2,6~.0~11,15~]octadeca-3,8-dien-5-one C28H32O6 详情 详情
(XLIV) 55278 [4-(acetyloxy)-3-methoxyphenyl]acetic 2,4,6-trichloro-1-benzenecarboxylic anhydride C18H13Cl3O6 详情 详情
(XLV) 55279 [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-15-isopropenyl-4,17-dimethyl-5-oxo-12,14,18-trioxapentacyclo[11.4.1.0~1,10~.0~2,6~.0~11,15~]octadeca-3,8-dien-8-yl]methyl 2-[4-(acetyloxy)-3-methoxyphenyl]acetate C39H42O10 详情 详情
Extended Information