Improved catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate: application to various 1-hydroxy sugars.
Efficient catalytic and stereoselective glycosylation was achieved by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acid in the presence of a glycosyl acceptor and 5A molecular sieves. Catalytic one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was achieved stereoselectively by reaction with trichloroacetyl isocyanate, followed by activation with a catalytic amount of activators.
Shirahata
Tatsuya
T
School of Pharmacy, Kitasato University 5-9-1, Shirokane, Minato-ku, Tokyo, Japan.
Matsuo
Jun-ichi
J
Teruya
Satoko
S
Hirata
Nozomu
N
Kurimoto
Taku
T
Akimoto
Nanao
N
Sunazuka
Toshiaki
T
Kaji
Eisuke
E
Omura
Satoshi
S
D002219:Carbamates / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
D002219:Carbamates; D002241:Carbohydrates