NDLI: Functional group tolerance in organocatalytic regioselective acylation of carbohydrates.

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Functional group tolerance in organocatalytic regioselective acylation of carbohydrates.

Content Provider	Semantic Scholar
Author	Ueda, Yoshihiro Muramatsu, Wataru Mishiro, Kenji Furuta, Takumi Kawabata, Takeo
Copyright Year	2009
Abstract	Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R' = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by 1 was found to be high.
Starting Page	397
Ending Page	399
Page Count	3
File Format	PDF HTM / HTML
Alternate Webpage(s)	https://repository.kulib.kyoto-u.ac.jp/dspace/bitstream/2433/139191/1/10_8-9.pdf
Alternate Webpage(s)	http://www.kuicr.kyoto-u.ac.jp/sites/sozai/icr/report/2010/10_8-9.pdf
PubMed reference number	19908913v1
Alternate Webpage(s)	https://doi.org/10.1021/jo901569v
DOI	10.1021/jo901569v
Journal	The Journal of organic chemistry
Volume Number	74
Issue Number	22
Language	English
Access Restriction	Open
Subject Keyword	Acylation Anhydrides Carbohydrates Chorionic Gonadotropin, beta Subunit, Human Disaccharides Gallic acid Hydroxyl Radical Occur (action) Thioctic Acid alpha-Mannosidosis cinnamic acid preparation hydroxyl group
Content Type	Text
Resource Type	Article

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