(2R,4aR,7R,8R,8aS)-6-(allyloxy)-7,8-bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine; (2R,4aR,7R,8R,8aS)-6-(allyloxy)-7-(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-yl benzyl ether -Drug Synthesis Database

【结构式】

【分子编号】40485

【品名】(2R,4aR,7R,8R,8aS)-6-(allyloxy)-7,8-bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine; (2R,4aR,7R,8R,8aS)-6-(allyloxy)-7-(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-yl benzyl ether

【CA登记号】

【分子式】C₂₅H₃₀O₆

【分子量】426.5096

【元素组成】C 70.4% H 7.09% O 22.51%

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：(G)

The reaction of D-glucopyranose (A) with allyl alcohol (B) by means of HCl gives glucoside (C), which is treated with acetaldehyde diethylacetal (D) and TsOH in dichloromethane to yield the 4,6-O-ethylideneglucoside (E). Reaction of (E) with benzyl bromide (F), by means of NaH in DMF, affords the 2,3-di-O-benzyl-4,6-O-ethylideneglucoside (G), which is treated with potassium tert-butoxide and with HgO, HgCl2 to give the fully protected sugar (III).

参考文献中间体

合成目标

【1】 Vemishetti, P.; Sleezer, P.D.; Dillon, J.L.; Discordia, R.P.; Hartung, K.B.; Silverberg, L.J.; Efficient synthesis of the anticancer drug etoposide 4'-phosphate: Use of benzylic ether-protecting groups on the carbohydrate segment. Org Process Res Dev 2000, 4, 1, 34.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	12234	2-Propen-1-ol; Allyl alcohol	107-18-6	C₃H₆O	详情	详情
(F)	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
(A)	23276	5-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol		C₆H₁₂O₆	详情	详情
(E)	40484	(2R,4aR,7R,8R,8aS)-6-(allyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol		C₁₁H₁₈O₆	详情	详情
(G)	40485	(2R,4aR,7R,8R,8aS)-6-(allyloxy)-7,8-bis(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine; (2R,4aR,7R,8R,8aS)-6-(allyloxy)-7-(benzyloxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-yl benzyl ether		C₂₅H₃₀O₆	详情	详情
(D)	40486	1-ethoxyethyl ethyl ether; 1,1-diethoxyethane	105-57-7	C₆H₁₄O₂	详情	详情
(III)	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
(C)	40483	(3R,4S,5S,6R)-2-(allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol		C₉H₁₆O₆	详情	详情

Extended Information