An efficient synthesis of cyclodextrin-based carbohydrate cluster compounds

David A. Fulton; J. Fraser Stoddart

doi:10.1021/ol005668x

An efficient synthesis of cyclodextrin-based carbohydrate cluster compounds

David A. Fulton^*, J. Fraser Stoddart

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

90 Scopus citations

Abstract

The photoaddition of the thiol 2,3,4,6-tetra-O-acetyl-β-D-1-thioglucopyranose to the allyl ether functions of per-2-allyl-, per-6-allyl-, and per-2,6-diallyl-β-cyclodextrin derivatives provides a remarkably simple and efficient way for attaching glucopyranose units onto (1) the secondary face, as well as (2) the primary face, of β-cyclodextrin - not to mention (3) both the primary and secondary faces, simultaneously - in yields of up to 70%.

Original language	English (US)
Pages (from-to)	1113-1116
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	8
DOIs	https://doi.org/10.1021/ol005668x
State	Published - Apr 20 2000

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol005668x

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AB - The photoaddition of the thiol 2,3,4,6-tetra-O-acetyl-β-D-1-thioglucopyranose to the allyl ether functions of per-2-allyl-, per-6-allyl-, and per-2,6-diallyl-β-cyclodextrin derivatives provides a remarkably simple and efficient way for attaching glucopyranose units onto (1) the secondary face, as well as (2) the primary face, of β-cyclodextrin - not to mention (3) both the primary and secondary faces, simultaneously - in yields of up to 70%.

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An efficient synthesis of cyclodextrin-based carbohydrate cluster compounds

Abstract

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