Synthesis 2006(9): 1415-1418  
DOI: 10.1055/s-2006-926434
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Synthesis of Neosaccharides: 2,6′-and 3,6′-Ether-Linked Sugars

Hideyo Takahashi, Haruhiko Mitsuzuka, Kazusa Nishiyama, Shiro Ikegami*
Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-0195, Japan
Fax: +81(426)851870; e-Mail: shi-ike@pharm.teikyo-u.ac.jp;
Further Information

Publication History

Received 28 September 2005
Publication Date:
11 April 2006 (eFirst)

Abstract

A novel synthesis of the 2,6′-O-linkage of methyl α-d-glucoside and methyl α-d-mannoside was developed based on an acetalization-reduction approach. Utilizing this approach, the 3,6′-O-linkage of methyl α-d-glucosides was also obtained. It is noteworthy that the reductive etherification of secondary alcohols and the C6-aldehyde of carbohydrates proceeded efficiently.

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2

We propose here that the sugars which are not linked by anomeric linkages should be called ‘neo-saccharides’. Thus the 6,6′-ether-linked sugar should be called a ‘neo-6,6′-O-saccharide’.

7

We have no definite information on this over-reduction because the reaction was not clean. We abandoned further investigation of this reduction with bulky silanes.

9

The cyclic acetal composed of pyranosides was unexpectedly stable. Further investigations to employ such connections in the novel linkage of sugars are currently underway in our laboratory.

10

The stereochemical outcome was accurately determined from the NMR spectrum of its acetate.