Ring Cleavage Reactions of Methyl α-D-Allopyranoside Derivatives with Phenylboron Dichloride and Triethylsilane 英文参考文献.docVIP

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Ring Cleavage Reactions of Methyl α-D-Allopyranoside Derivatives with Phenylboron Dichloride and Triethylsilane 英文参考文献.doc

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Ring Cleavage Reactions of Methyl α-D-Allopyranoside Derivatives with Phenylboron Dichloride and Triethylsilane 英文参考文献

Molecules 2011, 16, 10303-10313; doi:10.3390/molecules161210303 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Ring Cleavage Reactions of Methyl α-D-Allopyranoside Derivatives with Phenylboron Dichloride and Triethylsilane Masaru Kojima *, Yutaka Nakamura, Yuusuke Ito and Seiji Takeuchi Niigata University of Pharmacy and Applied Life Sciences, 265-1 Higashijima, Akiha-ku, Niigata 956-8603, Japan * Author to whom correspondence should be addressed; E-Mail: masaru@nupals.ac.jp; Tel.: +81-250-25-5165; Fax: +81-250-25-5021. Received: 31 October 2011; in revised form: 25 November 2011 / Accepted: 5 December 2011 / Published: 13 December 2011 Abstract: In the course of our studies on the regioselective carbon-oxygen bond cleavage of the benzylidene acetal group of hexopyranosides with a reducing agent, we found that a combination of a Lewis acid and a reducing agent triggered a ring-opening reaction of the pyranose ring of methyl α-D-allopyranosides. The formation of an acyclic boronate ester by the attachment of a hydride ion at C-1 indicated that the unexpected endocyclic cleavage of the bond between the anomeric carbon atom and the pyranose ring oxygen atom proceeded via an oxacarbenium ion intermediate produced by the chelation between O5/O6 of the pyranoside and the Lewis acid, followed by nucleophile substitution with a hydride ion at C1. Keywords: methyl α-D-allopyranoside; endocyclic cleavage; phenylboron dichloride; triethylsilane 1. Introduction Lewis-acid-induced regioselective carbon-oxygen bond cleavage of the benzylidene acetal group of hexopyranosides with a reducing agent is an important reaction in carbohydrate chemistry for the syntheses of complex oligosaccharides and glycoconjugates. Until now, various reagent systems [1-12] and investigations of the detailed mechanistic pathway [13,14] have been reported for the regioselective reduction of 4,6-O-benzylidene acetal gr