The first hetero-bifunctionalization of the secondary face of β-cyclodextrin: selective and efficient conversion of the A-ring of a 2A,2B-disulfonate to 2A,3A-epoxymannoside

Makoto Fukudome; Yuji Sugimoto; De-Qi Yuan; Kahee Fujita

doi:10.1039/B502573G

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The first hetero-bifunctionalization of the secondary face of β-cyclodextrin: selective and efficient conversion of the A-ring of a 2^A,2^B-disulfonate to 2^A,3^A-epoxymannoside

Makoto Fukudome,^a Yuji Sugimoto,^a De-Qi Yuan^a and Kahee Fujita^a

Author affiliations

^a Department of Molecular Medicinal Sciences, Graduate School of Biomedical Sciences, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan
E-mail: fujita@net.nagasaki-u.ac.jp
Fax: +81 95 8192423
Tel: +81 95 8192423

Abstract

The A-ring of 2^A,2^B-O,O-di(mesitylenesulfonyl)-β-cyclodextrin was converted to 2^A,3^A-epoxymannoside without affecting the other sulfonylated residue, which affords the first approach to hetero-bifunctionalization at the secondary hydroxyl side of cyclodextrins.

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Article information

DOI: https://doi.org/10.1039/B502573G
Article type: Communication
Submitted: 22 Feb 2005
Accepted: 22 Apr 2005
First published: 18 May 2005

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Chem. Commun., 2005, 3168-3170

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The first hetero-bifunctionalization of the secondary face of β-cyclodextrin: selective and efficient conversion of the A-ring of a 2^A,2^B-disulfonate to 2^A,3^A-epoxymannoside

M. Fukudome, Y. Sugimoto, D. Yuan and K. Fujita, Chem. Commun., 2005, 3168 DOI: 10.1039/B502573G

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Chemical Communications

The first hetero-bifunctionalization of the secondary face of β-cyclodextrin: selective and efficient conversion of the A-ring of a 2^A,2^B-disulfonate to 2^A,3^A-epoxymannoside

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The first hetero-bifunctionalization of the secondary face of β-cyclodextrin: selective and efficient conversion of the A-ring of a 2^A,2^B-disulfonate to 2^A,3^A-epoxymannoside

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