TY - JOUR
T1 - Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters
AU - Carvalho, Ivone
AU - Scheuerl, Shona L.
AU - Kartha, K. P. Ravindranathan
AU - Field, Robert A.
N1 - Funding Information:
These studies were supported by the MRC and the Weston Foundation. Support in the form of a research leave fellowship from FAPESP is gratefully acknowledged (IC). We thank Julia Bilke for performing some preliminary glycosylation experiments. We are indebted to the EPSRC Mass Spectrometry Service Centre, Swansea for invaluable support.
PY - 2003/5/1
Y1 - 2003/5/1
N2 - Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-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 β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).
AB - Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-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 β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).
KW - Benzyl ester
KW - Free carboxylic acid
KW - Glycosylation
KW - Mercuric bromide
KW - Serine
KW - Threonine
UR - http://www.scopus.com/inward/record.url?scp=0037403301&partnerID=8YFLogxK
U2 - 10.1016/S0008-6215(03)00071-5
DO - 10.1016/S0008-6215(03)00071-5
M3 - Article
C2 - 12706969
AN - SCOPUS:0037403301
SN - 0008-6215
VL - 338
SP - 1039
EP - 1043
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 10
ER -