Boronic Acid-Catalyzed Regioselective Koenigs–Knorr-Type Glycosylation

Boronic acid-catalyzed regioselective Koenigs–Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proce...

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Published inJournal of organic chemistry Vol. 86; no. 8; pp. 5973 - 5982
Main Authors Shimada, Naoyuki, Sugimoto, Tomoya, Noguchi, Mao, Ohira, Chikako, Kuwashima, Yutaro, Takahashi, Naoya, Sato, Noriko, Makino, Kazuishi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.04.2021
Amer Chemical Soc
Subjects
boronic acids
catalysts
Chemistry
Chemistry, Organic
glycols
glycosidic linkages
glycosylation
organic chemistry
Physical Sciences
regioselectivity
Science & Technology
silver oxide
TRANSIENT MASKING
ACTIVATION
OLIGOSACCHARIDES
ACYLATION
NATURAL-PRODUCTS
ALKYLATION
HEXOPYRANOSIDE
GLYCOSIDATIONS
SILYLATION
CARBOHYDRATE-CHEMISTRY
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Summary:Boronic acid-catalyzed regioselective Koenigs–Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proceed smoothly, which enables construction of a 1,2-trans glycosidic linkage with high regioselectivities. This is the first example of the use of a boronic acid catalyst to initiate regioselective glycosylation via the activation of cis-vicinal diols in glycosyl acceptors.
Bibliography:KAKEN
ObjectType-Article-1
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.1c00130