Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 83-92 |
| Number of pages | 10 |
| Journal | Carbohydrate Research |
| Volume | 325 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2000 Apr 7 |
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Keywords
- Acidic tetrasaccharide
- Anti-ulcer pectic polysaccharide
- Bupleurum falcatum
- Chemical synthesis
ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry
Cite this
Synthesis of a model compound related to an anti-ulcer pectic polysaccharide. / Maruyama, Michiko; Takeda, Tadahiro; Shimizu, Noriko; Hada, Noriyasu; Yamada, Haruki.
In: Carbohydrate Research, Vol. 325, No. 2, 07.04.2000, p. 83-92.Research output: Contribution to journal › Article
}
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
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
UR - http://www.scopus.com/inward/record.url?scp=0034616094&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0034616094&partnerID=8YFLogxK
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 -