Stereoselective synthesis of α- And β-glycofuranosyl amides by traceless ligation of glycofuranosyl azides

Nisic F.; Speciale G.; Bernardi A.

首页> 外文期刊>Chemistry: A European journal >Stereoselective synthesis of α- And β-glycofuranosyl amides by traceless ligation of glycofuranosyl azides

【24h】

Stereoselective synthesis of α- And β-glycofuranosyl amides by traceless ligation of glycofuranosyl azides

机译：糖呋喃糖基叠氮化物的无痕连接，立体选择性合成α-和β-呋喃呋喃糖基酰胺

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

A highly stereoselective synthesis of α- or β-glycofuranosyl amides based on the traceless Staudinger ligation of glycofuranosyl azides of the galacto, ribo, and arabino series with 2-diphenylphosphanyl-phenyl esters has been developed. Both α- and β-isomers can be obtained with excellent selectivity from a common, easily available precursor. The process does not depend on the anomeric configuration of the starting azide but appears to be controlled by the C2 configuration and by the protection/deprotection state of the substrates. A mechanistic interpretation of the results, supported by ~(31)P NMR experiments, is offered and merged with our previous mechanistic analysis of pyranosyl azide ligation reactions.

机译：基于半乳糖，核糖和阿拉伯糖系列的呋喃呋喃糖基叠氮化物与2-二苯基膦酰基-苯基酯的无痕Staudinger连接，已经开发了α-或β-呋喃呋喃糖基酰胺的高度立体选择性合成。从常见的，容易获得的前体中，可以出色的选择性获得α-和β-异构体。该方法不取决于起始叠氮化物的端基构型，而是似乎受C2构型和底物的保护/脱保护状态控制。提供了〜（31）P NMR实验支持的结果的机理解释，并与我们以前的吡喃糖基叠氮化物连接反应的机理分析合并。

著录项

来源
《Chemistry: A European journal》 |2012年第22期|共12页
作者
Nisic F.; Speciale G.; Bernardi A.;
展开▼
作者单位

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类
关键词
azides; carbohydrates; glycomimetics; neo-glycoconjugates; Staudinger ligation; stereoselective synthesis;

机译：叠氮化物;碳水化合物;糖模拟物;新糖共轭物;施陶丁格连接;立体选择性合成;

相似文献

外文文献
中文文献
专利

1. Stereoselective synthesis of α- And β-glycofuranosyl amides by traceless ligation of glycofuranosyl azides [J] . Nisic F., Speciale G., Bernardi A. Chemistry: A European journal . 2012,第22期

机译：糖呋喃糖基叠氮化物的无痕连接，立体选择性合成α-和β-呋喃呋喃糖基酰胺
2. Stereoselective synthesis of glycosyl amides by traceless Staudinger ligation of unprotected glycosyl azides [J] . Nisic F, Bernardi A Carbohydrate research . 2008,第10a11期

机译：通过无保护的糖基叠氮化物的无痕施陶丁格连接，立体选择性地合成糖基酰胺
3. Traceless staudinger ligation of glycosyl azides with triaryl phosphines: Stereoselective synthesis of glycosyl amides [J] . Bianchi A, Bernardi A The Journal of Organic Chemistry . 2006,第12期

机译：糖基叠氮化物与三芳基膦的无痕施陶丁格连接：糖基酰胺的立体选择性合成
4. Backbone amide linker (BAL)/fmoc synthesis of peptide thioester intermediates required for native chemical ligation [C] . Dominique Lelievre, George Barany the International Peptide Symposium . 2001

机译：骨干酰胺链接剂（BAL）/ FMOC本土化学连接所需的肽硫酯中间体
5. A photolabile backbone amide linker for the solid-phase synthesis of cyclic peptides. Cysteine-free native chemical ligation. Synthesis and biological evaluation of a library of resveratrol analogues. [D] . Kang, Soo Sung. 2009

机译：光不稳定的主链酰胺接头，用于固相合成环状肽。无半胱氨酸的天然化学连接。白藜芦醇类似物文库的合成和生物学评估。
6. Chemo-and Stereoselective Transition-Metal-Free Aminationof Amides with Azides [O] . Veronica Tona, §, Aurélien de la Torre, -1

机译：化学-和立体选择性过渡无金属胺化叠氮化物的酰胺
7. Traceless Staudinger Ligation of Glycosyl Azides with Triaryl Phosphines: Stereoselective Synthesis of Glycosyl Amides [O] . -1

机译：用三芳基磷酸酯的无糖基叠糖酰胺的无痕巨大的Staudinger结扎：糖基酰胺的立体选择性合成
8. Enolboration 7. Dicyclohexyliodoborane, a Highly Stereoselective Reagent For theEnolboration Of Tertiary Amides. Effects of Solvent And Aldolization Temperature on Stereochemistry Achieving the Stereoselective Synthesis of Either Syn or Anti Aldols [R] . Ganesan, K., Brown, H. C. 1994

机译：配合7.二环己基碘硼烷，一种高立体选择性试剂，用于叔酰胺的合成。溶剂和醛醇化温度对立体化学实现syn或anti aldols立体选择性合成的影响

Stereoselective synthesis of α- And β-glycofuranosyl amides by traceless ligation of glycofuranosyl azides

摘要

著录项

相似文献

相关主题

期刊订阅