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【结 构 式】

【分子编号】40486

【品名】1-ethoxyethyl ethyl ether; 1,1-diethoxyethane

【CA登记号】105-57-7

【 分 子 式 】C6H14O2

【 分 子 量 】118.17596

【元素组成】C 60.98% H 11.94% O 27.08%

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:(D)

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).

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
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