TY - JOUR
T1 - A Chemo-Enzymatic Synthesis of D-Allosamine Derivatives from Tri-O-acetyl- D-glucal
AU - Sugai, Takeshi
AU - Okazaki, Hanako
AU - Kuboki, Atsuhito
AU - Ohta, Hiromichi
PY - 1997/10
Y1 - 1997/10
N2 - N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O-acetyl-D-glucal based on lipase-catalyzed selective protection of primary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacetimidates, and stereo- selective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase- catalyzed acetylation occurred in a high yield (> 90%) exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.
AB - N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O-acetyl-D-glucal based on lipase-catalyzed selective protection of primary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacetimidates, and stereo- selective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase- catalyzed acetylation occurred in a high yield (> 90%) exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.
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U2 - 10.1246/bcsj.70.2535
DO - 10.1246/bcsj.70.2535
M3 - Article
AN - SCOPUS:0000834727
SN - 0009-2673
VL - 70
SP - 2535
EP - 2540
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 10
ER -