(5R,5aR,8aR,9S)-9-[[(2R,4aR,6S,7R,8R,8aS)-7,8-bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one -Drug Synthesis Database

【结构式】

【分子编号】41891

【品名】(5R,5aR,8aR,9S)-9-[[(2R,4aR,6S,7R,8R,8aS)-7,8-bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

【CA登记号】

【分子式】C₄₃H₄₄O₁₃

【分子量】768.81456

【元素组成】C 67.18% H 5.77% O 27.05%

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：(IV)

The condensation of dibenzyl-sugar (II) with 4'-demethyl-epipodophyllotoxin (I) by means of BF3·Et2O in acetonitrile gives a mixture of the alpha and beta coupled products (IV) + (III), which by crystallization in dichloromethane/methanol afforded pure diastereomer beta (III). Finally this compound is debenzylated by hydrogenolysis with H2 over Pd/C in THF.

参考文献中间体

合成目标

【1】 Silverberg, L.J.; et al.; A crystallization-induced steroselective glycosidation reaction in the synthesis of the anticancer drug etoposide. Org Lett 2000, 2, 21, 3281.

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)	13053	(5R,5aR,8aR,9S)-9-Hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one	6559-91-7	C₂₁H₂₀O₈	详情	详情
(II)	13055	(2R,4aR,6S,7R,8R,8aS)-7,8-Bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-ol		C₂₂H₂₆O₆	详情	详情
(III)	41886	(5R,5aR,8aR,9S)-9-[[(2R,4aR,6R,7R,8R,8aS)-7,8-bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one		C₄₃H₄₄O₁₃	详情	详情
(IV)	41891	(5R,5aR,8aR,9S)-9-[[(2R,4aR,6S,7R,8R,8aS)-7,8-bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one		C₄₃H₄₄O₁₃	详情	详情

Extended Information