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【结 构 式】

【分子编号】34970

【品名】(1R,11R,12R,15R)-15-[(benzyloxy)methyl]-11-(3,4,5-trimethoxyphenyl)-5,7,14-trioxatetracyclo[10.2.1.0(2,10).0(4,8)]pentadeca-2(10),3,8-trien-13-one

【CA登记号】

【 分 子 式 】C29H28O8

【 分 子 量 】504.53652

【元素组成】C 69.04% H 5.59% O 25.37%

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:(XV)

The isomerization of trans-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]benzodioxole-6-carboxylic acid ethyl ester (XI) with LDA gives the corresponding cis isomer (XII), which is treated with trimethylsilyl triflate yielding the silylated enol ether (XIII). The reaction of (XIII) with benzyloxymethyl chloride and TiCl4 affords the benzyloxymethyl derivative (XIV), which is reduced at the ketonic group with LiBH4 giving the lactone (XV). The debenzylation of (XV) with H2 over Pd/C yields the carbinol (XVI), which is rearranged to the target compound with DCC in acidic medium.

1 Kaneko, T.; et al.; Total synthesis of (±) podophyllotoxin. Tetrahedron Lett 1987, 28, 5, 517.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
14560 Benzyl chloromethyl ether; 1-[(chloromethoxy)methyl]benzene 3587-60-8 C8H9ClO 详情 详情
(XI) 34966 ethyl (5R,6R)-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate C23H24O8 详情 详情
(XII) 34967 ethyl (5R,6S)-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate C23H24O8 详情 详情
(XIII) 34968 ethyl (5R,6R)-5-(3,4,5-trimethoxyphenyl)-8-[(trimethylsilyl)oxy]-5,6-dihydronaphtho[2,3-d][1,3]dioxole-6-carboxylate C26H32O8Si 详情 详情
(XIV) 34969 ethyl (5R,6R,7R)-7-[(benzyloxy)methyl]-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate C31H32O9 详情 详情
(XV) 34970 (1R,11R,12R,15R)-15-[(benzyloxy)methyl]-11-(3,4,5-trimethoxyphenyl)-5,7,14-trioxatetracyclo[10.2.1.0(2,10).0(4,8)]pentadeca-2(10),3,8-trien-13-one C29H28O8 详情 详情
(XVI) 34971 (1R,11R,12R,15R)-15-(hydroxymethyl)-11-(3,4,5-trimethoxyphenyl)-5,7,14-trioxatetracyclo[10.2.1.0(2,10).0(4,8)]pentadeca-2(10),3,8-trien-13-one C22H22O8 详情 详情
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