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Synthesis 2010(1): 43-48
DOI: 10.1055/s-0029-1217073
DOI: 10.1055/s-0029-1217073
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Novel Glycosidation of α-d-Altropyranosides
Further Information
Received
21 July 2009
Publication Date:
26 October 2009 (online)
Publication History
Publication Date:
26 October 2009 (online)
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Abstract
A new glycosidation of α-d-altropyranosides, in which the 2-hydroxy group is not protected, was developed. The reaction proceeds via a 1,2-β-oxirane, which is formed in situ without extra steps for exchanging the 1-methoxy group to a more reactive leaving group. The glycoside bond of α-d-altropyranoside was shown to be weaker compared with those of α-d-glucopyranoside and α-d-mannopyranoside.
Key words
carbohydrates - glycosylations - epoxides - ring opening - d-altropyranoside
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Glycosidation of 2-alkylated altrosides resulted in lower yields.