Endo–Glycal的Phosphite-assisted和Michael加成反應

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Title:	Endo–Glycal的Phosphite-assisted和Michael加成反應 Phosphite-assisted and Michael Addition of Endo- glycal
Authors:	王思懿
Contributors:	藥物化學研究所碩士班
Keywords:	2,3不飽和醣苷烯丙基亞磷酸;醣加成反應 2,3-unsaturated glycosides;glycosylation;azepane;Intramolecular Michael addition
Date:	2011-08-01
Issue Date:	2011-10-17 16:58:11 (UTC+8)
Publisher:	中國醫藥大學
Abstract:	2,3不飽和醣苷可以成功地藉由烯丙基亞磷酸輔助的醣加成反應來進行合成。而Endo-Glycosyl 亞磷酸在加入催化量的氯化鋁以及各種的帶有氧的親核性試劑包括醇類及醣類可在溫和的條件下進行反應。最後，可得到期望中的α態含氧醣苷產物，其產率相當高並具有高度選擇性，其 α/β比率超過92/8。本文中介紹了一種新的合成路線，可望能從3,4,6-tri-O-acetyl-D-glucal為起始物合成出6-amino hex-1-en-3-uloses及azepane的衍生物。這個方法包括了從烯丙醇基團的氧化與疊氮基團的還原來合成6-amino hex-1-en-3-uloses。但可惜的是，我們無法從6-amino hex-1-en-3-uloses進行的分子內Michael加成反應得到azepane的衍生物。 2,3-unsaturated glycosides were successfully synthesized by means of allylic phosphite-assisted glycosylation. Endo-Glycosyl phosphite were treated with catalytic amount of AlCl3 and various O-nucleophiles including alcohols and sugars under the mild conditions. The desired α-O-glycosides products were obtained in good to excellent yields with high stereoselectivity(α/β?d92/8) . This paper also describes a new synthetic route towards 6-amino hex-1-en-3-uloses and azepane derivatives starting from 3,4,6-tri-O-acetyl-D-glucal. The method involves allylic alcohol was oxidated and azide group was reducted to afford the 6-amino hex-1-en-3-uloses. However, we can not afforded the azepane derivatives by Intramolecular Michael addition of 6-amino hex-1-en-3-uloses.
Appears in Collections:	[Graduate Institute of Pharmaceutical Chemistry] Theses & dissertations

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