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

被引：17

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：

070301 [无机化学];

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

共 8 条

[1]

Carey F.A., 2010, ORGANIC CHEM, P137

[2]

Diazidomethane Explosion [J].

Conrow, Raymond E. ;

Dean, W. Dennis .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (06) :1285-1286

[3]

A Simple SN2 Reaction for the Undergraduate Organic Laboratory [J].

Esteb, John J. ;

Magers, John R. ;

McNulty, LuAnne ;

Morgan, Paul ;

Wilson, Anne M. .

JOURNAL OF CHEMICAL EDUCATION, 2009, 86 (07) :850-852

[4]

Representation of the aceto-bromine glucose. [J].

Fischer, E .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1916, 49 :584-585

[5]

Stereoselective Synthesis of N-Glycosyl Amino Acids by Traceless Staudinger Ligation of Unprotected Glycosyl Azides [J].

Nisic, Filippo ;

Andreini, Manuel ;

Bernardi, Anna .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (33) :5744-5751

[6]

Chemical Probes for Labeling of the Bacterial Glucosaminidase NagZ via the Huisgen Cycloaddition [J].

Orth, Ronald ;

Pitscheider, Maximilian ;

Sieber, Stephan A. .

SYNTHESIS-STUTTGART, 2010, (13) :2201-2206

[7]

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide [J].

Temelkoff, DP ;

Norris, P ;

Zeller, M .

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 :O1975-O1976

[8]

The Conversion of L-Phenylalanine to (S)-2-Hydroxy-3-phenylpropanoic Acid: A Simple, Visual Example of a Stereospecific SN2 Reaction [J].

Van Draanen, Nanine A. ;

Hengst, Stephanie .

JOURNAL OF CHEMICAL EDUCATION, 2010, 87 (06) :623-624

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