Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters.
Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding beta-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding beta-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).
Carvalho
Ivone
I
Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Brazil.
Scheuerl
Shona L
SL
Ravindranathan Kartha
K P
KP
Field
Robert A
RA
D001554:Benzene / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D004952:Esters; D005025:Ethylene Dichlorides / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008628:Mercury / Q000737:chemistry; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry*; D013912:Threonine / Q000737:chemistry*
D001965:Bromides; D002264:Carboxylic Acids; D004952:Esters; D005025:Ethylene Dichlorides; D005960:Glucosides; D013912:Threonine; D012694:Serine; D008628:Mercury; D001554:Benzene