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 -Drug Synthesis Database

【结构式】

【分子编号】34969

【品名】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

【CA登记号】

【分子式】C₃₁H₃₂O₉

【分子量】548.58968

【元素组成】C 67.87% H 5.88% O 26.25%

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：(XIV)

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.

参考文献中间体

合成目标

【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

Extended Information