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Molecules 2017, 22(3), 429; doi:10.3390/molecules22030429

A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group

1
Oceanography Section, Science Research Center, Kochi University, Otsu, Nankoku-shi, Kochi 783-8502, Japan
2
Laboratory of Natural Products Chemistry, Faculty of Science, Kochi University, Akebono-cho, Kochi-shi, Kochi 780-8520, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Shunichi Fukuzumi
Received: 6 January 2017 / Revised: 27 February 2017 / Accepted: 3 March 2017 / Published: 8 March 2017
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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Abstract

A new direct method for β-selective glycosylation with an N-acetylglucosamine (GlcNAc) donor was developed. This substrate, which can be readily prepared from commercially available GlcNAc in two steps, contains a 4-O-tert-butyldimethylsilyl (TBDMS) protecting group as a key component. We found that this functionality could have a favorable effect on the reactivity of the GlcNAc donor. Glycosylation with the armed donor using primary alcohols in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) in 1,2-dichloroethane smoothly gave the desired coupling products in good yields with complete β-selectivity, while sterically hindered acceptors were less efficient. View Full-Text
Keywords: N-acetylglucosamine; β-selective glycosylation; remote protecting group effect; O-TBDMS protecting group N-acetylglucosamine; β-selective glycosylation; remote protecting group effect; O-TBDMS protecting group
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Tanaka, H.; Hamaya, Y.; Kotsuki, H. A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group. Molecules 2017, 22, 429.

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