Selective acetylation of benzyl α-D-mannopyranoside, benzyl-β-D-glucopyranoside, and benzyl β-D-galactopyranoside☆
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Add time:08/28/2019 Source:sciencedirect.com
Acetylation of benzyl α-D-mannopyranoside with acetic anhydride-sodium acetate at room temperature gave crystalline benzyl 2,3,6-tri-O-acetyl-α-D-manno-pyranoside (25%) and benzyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (≈65%). Similar esterification of benzyl β-D-glucopyranoside yielded the crystalline benzyl 2,4,6-triacetate (66%), whereas the corresponding galactopyranoside gave the crystalline 3,4,6-, 2,3,6-, and 2,4,6-triacetates (3, 25, and 9%. respectively). The structures of these compounds were established by methylation with diazomethane-boron trifluoride etherate and were confirmed by n.m.r. studies.
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