(3aS,6S,7R,7aS)-6-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】48968

【品名】(3aS,6S,7R,7aS)-6-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate

【CA登记号】

【分子式】C₁₇H₂₂O₆

【分子量】322.35808

【元素组成】C 63.34% H 6.88% O 29.78%

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：(V)

Synthesis of intermediate monosaccharide (VI): The reaction of L-arabinose (I) with benzyl alcohol and HCl (gas) gives 1-O-benzyl-L-arabinose (II), which is treated with 2,2-dimethoxypropane (III) and TsOH to yield the 3,4-O-isopropylidene derivative (IV). The selective acetylation of (IV) with Ac2O and pyridine affords the 2-O-acetyl derivative (V), which is finally treated with HOAc in hot water to provide the intermediate 2-O-acetyl-1-O-benzyl-L-arabinose (VI).

参考文献中间体

合成目标

【1】 Deng, S.; et al.; First total synthesis of an exceptionally potent antitumor saponin, OSW-1. J Org Chem 1999, 64, 1, 202.

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)	17520	(3R,4S,5S)tetrahydro-2H-pyran-2,3,4,5-tetrol; L-(+)-Arabinose	7296-56-2	C₅H₁₀O₅	详情	详情
(II)	48966	2-Benzyloxytetrahydropyran-3,4,5-triol		C₁₂H₁₆O₅	详情	详情
(III)	10722	1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane	77-76-9	C₅H₁₂O₂	详情	详情
(IV)	48967	(3aS,6S,7R,7aR)-6-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol		C₁₅H₂₀O₅	详情	详情
(V)	48968	(3aS,6S,7R,7aS)-6-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate		C₁₇H₂₂O₆	详情	详情
(VI)	48969	(2S,3R,4S,5S)-2-(benzyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl acetate		C₁₄H₁₈O₆	详情	详情

Extended Information