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Synthesis 2013; 45(14): 1946-1949
DOI: 10.1055/s-0033-1339174
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

4′,6′-O-Benzylidene- and 4′,6′-O-p-Methoxybenzylidene-α,β-cellobiose and Their Hexa-O-β-benzoyl Derivatives

Xiaowei Lu
NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA   Fax: +1(301)4805703   Email: kpn@helix.nih.gov
,
Deepak Sail
NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA   Fax: +1(301)4805703   Email: kpn@helix.nih.gov
,
Pavol Kováč*
NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA   Fax: +1(301)4805703   Email: kpn@helix.nih.gov
› Author Affiliations
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Publication History

Received: 26 March 2013

Accepted after revision: 07 May 2013

Publication Date:
26 June 2013 (online)

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Abstract

The preparation of 4′,6′-O-benzylidenecellobiose has been improved and its p-methoxybenzylidene counterpart was prepared in a similar way. As with other alkylidene derivatives of sugars, the corresponding per-O-benzoates are versatile intermediates in carbohydrate synthesis, allowing, after hydrolytic cleavage or opening of the phenylidene ring, regioselective manipulation of hydroxyl groups in cellobiose, or access to various derivatives of lactose.

Key words

synthetic methods - carbohydrate chemistry - protecting groups - regioselectivity

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