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【结 构 式】

【药物名称】SB-RA-31012011

【化学名称】3-Methoxybenzoic acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,9,12b-tris(acetoxy)-4-[3-(4-benzoylphenyl)-2(E)-propenoyloxy]-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl ester

【CA登记号】

【 分 子 式 】C50H52O15

【 分 子 量 】892.96294

【开发单位】Roswell Park Memorial Inst. (Originator), State University of New York,Stony Brook (Originator)

【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS

合成路线1

10-Deacetylbaccatin III (I) was protected by treatment with triethylsilyl chloride and imidazole, and the resulting trisilylated compound (II) was debenzoylated to diol (III) by using Red-Al(R). Coupling of (III) with m-anisic acid (IV) yielded the m-methoxybenzoate ester (V). Complete desilylation of (V), followed by selective resilylation at C-7 with triethylsilyl chloride, furnished (VI). Acylation at C-10 and C-13 by means of Ac2O and DMAP, followed by desilylation, gave the modified baccatin (VII).

1 Strum, M.; et al.; Synthesis and SAR of new taxane reversal agents. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 131.
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) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 51201 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C47H78O10Si3 详情 详情
(III) 51202 (1S,2S,3R,7R,9S,10S,12R,15S)-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-4-yl acetate C40H74O9Si3 详情 详情
(IV) 28559 m-Anisic acid; 3-Methoxybenzoic acid 586-38-9 C8H8O3 详情 详情
(V) 51203 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C48H80O11Si3 详情 详情
(VI) 51204 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C36H52O11Si 详情 详情
(VII) 51205 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-tris(acetoxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C34H42O13 详情 详情

合成路线2

Heck coupling between 4-bromobenzophenone (VIII) and methyl acrylate (IX) in the presence of palladium diacetate gave the unsaturated ester (X). Subsequent basic hydrolysis of the methyl ester group of (X) yielded p-benzoylcinnamic acid (XI). The title compound was then obtained by the coupling of acid (XI) with the precursor baccatin (VII) in the presence of EDC and DMAP.

1 Strum, M.; et al.; Synthesis and SAR of new taxane reversal agents. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 131.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 51205 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-tris(acetoxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C34H42O13 详情 详情
(VIII) 18447 (4-bromophenyl)(phenyl)methanone 90-90-4 C13H9BrO 详情 详情
(IX) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(X) 18449 methyl (E)-3-(4-benzoylphenyl)-2-propenoate C17H14O3 详情 详情
(XI) 18450 (E)-3-(4-benzoylphenyl)-2-propenoic acid C16H12O3 详情 详情
Extended Information