TY - JOUR
T1 - Synthesis of a model compound related to an anti-ulcer pectic polysaccharide
AU - Maruyama, Michiko
AU - Takeda, Tadahiro
AU - Shimizu, Noriko
AU - Hada, Noriyasu
AU - Yamada, Haruki
N1 - Funding Information:
The authors would like to thank Miss T. Naito for performing the microanalyses at Nagoya City University, Nagoya, Japan. This work was supported by a Grant-in-Aid for Scientific Research (No. 09672156) from the Ministry of Education, Science, Sports and Culture of Japan.
PY - 2000/4/7
Y1 - 2000/4/7
N2 - A stereocontrolled synthesis of the model compound for an anti-ulcer active polysaccharide (Bupleuran 2IIc) is described. Glycosidation of the disaccharide acceptor, 2-O-acetyl-3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate, with the disaccharide receptor, allyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside, using silver triflate (AgOTf) as a promoter gave the desired tetrasaccharide derivative, which was transformed into the acidic tetrasaccharide, corresponding to a segment of the rhamnogalacturonan (Bupleuran 2IIc) polysaccharide, propyl α-L-Rha-(1→4)-α-D-GalA-(1→2)-α-L-Rha-(1→4)-β-D-GalA, via removal of the corresponding ether and ester protecting groups, followed by oxidation. Copyright (C) 2000 Elsevier Science Ltd.
AB - A stereocontrolled synthesis of the model compound for an anti-ulcer active polysaccharide (Bupleuran 2IIc) is described. Glycosidation of the disaccharide acceptor, 2-O-acetyl-3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate, with the disaccharide receptor, allyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside, using silver triflate (AgOTf) as a promoter gave the desired tetrasaccharide derivative, which was transformed into the acidic tetrasaccharide, corresponding to a segment of the rhamnogalacturonan (Bupleuran 2IIc) polysaccharide, propyl α-L-Rha-(1→4)-α-D-GalA-(1→2)-α-L-Rha-(1→4)-β-D-GalA, via removal of the corresponding ether and ester protecting groups, followed by oxidation. Copyright (C) 2000 Elsevier Science Ltd.
KW - Acidic tetrasaccharide
KW - Anti-ulcer pectic polysaccharide
KW - Bupleurum falcatum
KW - Chemical synthesis
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U2 - 10.1016/S0008-6215(99)00315-8
DO - 10.1016/S0008-6215(99)00315-8
M3 - Article
C2 - 10795816
AN - SCOPUS:0034616094
VL - 325
SP - 83
EP - 92
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 2
ER -