Synthesis of a D-Glucopyranosyl Azide: Spectroscopic Evidence for Stereochemical Inversion in the SN2 Reaction

被引：15

作者：

Adesoye, Olumuyiwa G. ^{[1
]}

Mills, Isaac N. ^{[1
]}

Temelkoff, David P. ^{[1
]}

Jackson, John A. ^{[1
]}

Norris, Peter ^{[1
]}

机构：

[1] Youngstown State Univ, Dept Chem, Youngstown, OH 44555 USA

来源：

JOURNAL OF CHEMICAL EDUCATION | 2012年 / 89卷 / 07期

关键词：

Upper-Division Undergraduate; Laboratory Instruction; Organic Chemistry; Hands-On Learning/Manipulatives; Carbohydrates; Chirality/Optical Activity; Conformational Analysis; Mechanisms of Reactions; NMR Spectroscopy; Thin Layer Chromatography;

D O I：

10.1021/ed200596p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereospecific S(N)2 conversion of configurationally pure acetobromoglucose (2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide) to the corresponding beta-D-glucopyranosyl azide is a useful exercise in the advanced organic undergraduate teaching laboratory. The procedure is safe and suitable for small-scale implementation, and firm proof of the stereochernical change is obtained from H-1 NMR coupling constants. The exercise provides students with experience in using important chiral pool natural product derivatives, reaction analysis by TLC, as well as careful product isolation, purification, and spectroscopic identification.

引用

页码：943 / 945

页数：3

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