Some observations on the reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides with the borane trimethylamine-aluminium chloride reagent

被引：11

作者：

Daragics, Katalin ^{[1
]}

Szabo, Pal ^{[2
]}

Fuegedi, Peter ^{[1
]}

机构：

[1] Hungarian Acad Sci, Chem Res Ctr, Dept Carbohydrate Chem, H-1025 Budapest, Hungary

[2] Hungarian Acad Sci, Chem Res Ctr, Dept Biochem Pharmacol, H-1025 Budapest, Hungary

来源：

CARBOHYDRATE RESEARCH | 2011年 / 346卷 / 12期

关键词：

Benzylidene acetals; Reductive ring opening; Borane trimethylamine-aluminium chloride; By-products; Chelation; CARBOHYDRATE BENZYLIDENE ACETALS; ALPHA-D-GLUCOPYRANOSIDES; REGIOSELECTIVE PROTECTION; D-MANNOPYRANOSIDES; GLUCAN SYNTHESIS; D-GLUCOSE; CLEAVAGE; METHYL; CHELATION; HYDROGENOLYSIS;

D O I：

10.1016/j.carres.2011.04.046

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Reductive ring openings of 3-O-benzoyl-4,6-O-benzylidene-o-glucopyranosides with BH(3)center dot NMe(3)-AlCl(3) are accompanied by side reactions, such as debenzoylation and reduction of the benzoate to benzyl ether. This phenomenon was rationalized by aluminium chelate formation between the O-4 acetal and the benzoyl carbonyl group oxygens. It was also shown that these side reactions can be eliminated by using BH(3)center dot THF as the reducing agent. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1633 / 1637

页数：5

共 4 条

[1] Iodine-sodium cyanoborohydride-mediated reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides
Rao, Kaki Venkata
Patil, Premanand R.
Atmakuri, Sridhar
Kartha, K. P. Ravindranathan
CARBOHYDRATE RESEARCH, 2010, 345 (18) : 2709 - 2713
[2] Regio- and chemoselective reductive cleavage of 4,6-O-benzylidene-type acetals of hexopyranosides using BH3•THF-TMSOTf
Daragics, Katalin
Fuegedi, Peter
TETRAHEDRON LETTERS, 2009, 50 (24) : 2914 - 2916
[3] Cyanuric chloride/sodium borohydride: a new reagent combination for reductive opening of 4,6-benzylidene acetals of carbohydrates to primary alcohols
Tatina, Madhubabu
Yousuf, Syed Khalid
Aravinda, Subrayashastry
Singh, Baldev
Mukherjee, Debaraj
CARBOHYDRATE RESEARCH, 2013, 381 : 142 - 145
[4] Systematic Study of Regioselective Reductive Ring-Opening Reactions of 4,6-O-Halobenzylidene Acetals of Glucopyranosides
Mezo, Erika
Herczeg, Mihaly
Demeter, Fruzsina
Bereczki, Ilona
Csavas, Magdolna
Borbas, Aniko
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (18): : 12973 - 12987

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