Abstract
A stereocontrolled synthesis of Le x oligosaccharide derivatives using a facile one-pot, two-step glycosylation based on the "Armed-Disarmed" concept are described. The first coupling of phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)- 2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside (2) with phenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (3) using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) gave the trisaccharide (8) which was subjected to the second condensation without purification with several acceptors such as ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (4), ethyl 2,6-di-O-benzoyl-β-D-galactopyranoside (5), ethyl O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl- β-D-glucopyranoside (6), and ethyl O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl- β-D-glucopyranoside (7), to afford the desired Le x tetra- and pentasaccharides in good yields, respectively.
| Original language | English |
|---|---|
| Pages (from-to) | 673-681 |
| Number of pages | 9 |
| Journal | Journal of Carbohydrate Chemistry |
| Volume | 17 |
| Issue number | 4-5 |
| DOIs | |
| Publication status | Published - Jan 1 1998 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Organic Chemistry
Cite this
One-pot synthesis of Lewis X oligosaccharide derivatives using "armed-disarmed" coupling method. / Yoshida, Masahiro; Kiyoi, Takao; Tsukida, Takahiro; Kondo, Hirosato.
In: Journal of Carbohydrate Chemistry, Vol. 17, No. 4-5, 01.01.1998, p. 673-681.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - One-pot synthesis of Lewis X oligosaccharide derivatives using "armed-disarmed" coupling method
AU - Yoshida, Masahiro
AU - Kiyoi, Takao
AU - Tsukida, Takahiro
AU - Kondo, Hirosato
PY - 1998/1/1
Y1 - 1998/1/1
N2 - A stereocontrolled synthesis of Le x oligosaccharide derivatives using a facile one-pot, two-step glycosylation based on the "Armed-Disarmed" concept are described. The first coupling of phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)- 2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside (2) with phenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (3) using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) gave the trisaccharide (8) which was subjected to the second condensation without purification with several acceptors such as ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (4), ethyl 2,6-di-O-benzoyl-β-D-galactopyranoside (5), ethyl O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl- β-D-glucopyranoside (6), and ethyl O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl- β-D-glucopyranoside (7), to afford the desired Le x tetra- and pentasaccharides in good yields, respectively.
AB - A stereocontrolled synthesis of Le x oligosaccharide derivatives using a facile one-pot, two-step glycosylation based on the "Armed-Disarmed" concept are described. The first coupling of phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)- 2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside (2) with phenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (3) using N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) gave the trisaccharide (8) which was subjected to the second condensation without purification with several acceptors such as ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (4), ethyl 2,6-di-O-benzoyl-β-D-galactopyranoside (5), ethyl O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl- β-D-glucopyranoside (6), and ethyl O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl- β-D-glucopyranoside (7), to afford the desired Le x tetra- and pentasaccharides in good yields, respectively.
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UR - http://www.scopus.com/inward/citedby.url?scp=0032370019&partnerID=8YFLogxK
U2 - 10.1080/07328309808002344
DO - 10.1080/07328309808002344
M3 - Article
AN - SCOPUS:0032370019
VL - 17
SP - 673
EP - 681
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
SN - 0732-8303
IS - 4-5
ER -