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

【结 构 式】

【分子编号】47285

【品名】(5S)-5-(acetamido)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl di(tert-butyl) phosphate

【CA登记号】

【 分 子 式 】C28H40NO8P

【 分 子 量 】549.601302

【元素组成】C 61.19% H 7.34% N 2.55% O 23.29% P 5.64%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

The title phosphate ester was prepared from N-acetylcolchinol (I). Treatment of (I) with di-tert-butyl diethylphosphoramidite in the presence of tetrazole provided the phosphite ester (II), which was subsequently oxidized to phosphate (III) by means of MCPBA. The tert-butyl phosphate ester of (III) was finally cleaved using trifluoroacetic acid.

1 Dougherty, G. (Angiogene Pharmaceuticals Ltd.); Use of colchinol derivs. as vascular damaging agents. WO 9902166 .
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) 47283 N-[(5S)-3-hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide C20H23NO5 详情 详情
(II) 47284 (5S)-5-(acetamido)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl di(tert-butyl) phosphite C28H40NO7P 详情 详情
(III) 47285 (5S)-5-(acetamido)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl di(tert-butyl) phosphate C28H40NO8P 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

The reaction of colchicin (I) with aq. HCl at 100 C gives the monodemethylated compound (II), which is treated with H2O2 at 60 C to yield the dibenzocycloheptene derivative (III). The condensation of (III) with N,N-diethylphosphoramidic acid di-tert-butyl ester (IV) by means of tetrazole affords the phosphoric acid triester (V), which is finally treated with MCPBA to provide the target phosphoric acid monoester.

1 Blakey, D.C.; Davis, P.D.; Dougherty, G.J.; et al.; ZD6126: A novel vascular-targeting agent that causes selective destruction of tumor vasculature. Cancer Res 2002, 62, 24, 7247.
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) 18479 N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide 64-86-8 C22H25NO6 详情 详情
(II) 58655 N-[(7S)-10-hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide C21H23NO6 详情 详情
(III) 47283 N-[(5S)-3-hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide C20H23NO5 详情 详情
(IV) 58656   C12H28NO3P 详情 详情
(V) 47285 (5S)-5-(acetamido)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl di(tert-butyl) phosphate C28H40NO8P 详情 详情
Extended Information