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Treatment of O-acetyl-protected sugars with a methanolic solution of guanidine/guanidinium nitrate caused the removal of the acetyl groups (91-99% isolated yield), without affecting other protecting groups. Removal of O-benzoyl groups required a longer reaction time. Of special merit is the stability of the 2,2,2-trichloroethoxycarbonylamino (N-Troc) group under these weakly basic reaction conditions.
N-Troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, methyl 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranoside...
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