Tin-mediated equilibration of the benzoate esters of methyl 4,6-O-benzylidene-α-D-glucopyranoside

被引：12

作者：

Bredenkamp, MW ^{[1
]}

Spies, HSC ^{[1
]}

机构：

[1] Univ Stellenbosch, Dept Chem, ZA-7602 Matieland, South Africa

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 04期

关键词：

acylation; carbohydrates; NMR; tin compounds;

D O I：

10.1016/S0040-4039(99)02115-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective dibutyltin oxide-mediated benzoylation of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside at position 2 is not a post-acylation phenomenon as is the case with the equivalent benzoylation of phenylethyleneglycol. H-1 NMR temperature studies have shown that such equilibration occurs only above 85 degrees C in toluene-d(8) for the glucopyranoside. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：543 / 546

页数：4

共 6 条

[1] Polymorphism in the crystal structure of the cellulose fragment analogue methyl 4-O-methyl-β-D-glucopyranosyl-(1-4)-β-D-glucopyranoside
Rencurosi, A
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Jäger, C
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (22) : 4277 - 4281
[2] Organometallic supramolecular chemistry with monosaccharides:: Triethylammonium μ-chloro-bis{chloro(η5-cyclopentadienyl)-(methyl 4,6-O-benzylidene-β-D-glucopyranosidato-1κO2,1:2κO3)zirconate}
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[3] Synthesis of novel photolabile glycosides from methyl 4,6-O-(o-nitro)benzylidene-α-D-glycopyranosides
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MOLECULES, 2021, 26 (15):
[5] Highly stereoselective Lewis acid mediated conjugate radical additions to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4
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SYNLETT, 2000, (07) : 979 - 982
[6] Highly stereoselective α-alkylations, 1,4-additions, and one-pot 1,4-addition/α-methylations achieved on 4-O-acyl and 4-O-crotonyl derivatives of methyl 6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-α-D-glucopyranoside
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