Solid-phase synthesis of beta-mannosides.

David Crich; Mark Smith

doi:10.1021/ja011406u

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Solid-phase synthesis of beta-mannosides.

David Crich·Mark Smith

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Abstract

The linkage of S-phenyl 2,3-di-O-benzyl-alpha-D-thiomannopyranoside to a cross-linked polystyrene support in the form of its 4,6-O-polystyrylborinate ester is described. The activation of this polymer-supported mannosyl donor is achieved at -60 degrees C in dichloromethane in the presence of 2,4,6-tri-tert-butylpyrimidine with the combination 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. Addition of the donor alcohol at -60 degrees C followed by warming to room temperature and subsequent cleavage from the resin by gentle heating in aqueous acetone yields anomerically pure 2,3-di-O-benzyl-beta-D-mannopyranosides in excellent yield. Successful, diastereoselective coupling is demonstrated with a range of primary, secondary, and tertiary glycosyl acceptors, including typical carbohydrates and threonine derivatives.

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Carbohydrate Conformation Mannose Mannosides Polystyrenes Journal Article Research Support, U.S. Gov't, Non-P.H.S.Research Support, U.S. Gov't, P.H.S.

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David Crich, Mark Smith. 2002-07-31. Solid-phase synthesis of beta-mannosides.. https://doi.org/10.1021/ja011406u

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