One-pot synthesis of Lewis X oligosaccharide derivatives using "armed-disarmed" coupling method

Masahiro Yoshida, Takao Kiyoi, Takahiro Tsukida, Hirosato Kondo

Research output: Contribution to journalArticle

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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 languageEnglish
Pages (from-to)673-681
Number of pages9
JournalJournal of Carbohydrate Chemistry
Volume17
Issue number4-5
DOIs
Publication statusPublished - Jan 1 1998
Externally publishedYes

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Oligosaccharides
Galactose
Derivatives
Glycosylation
Trisaccharides
Purification
Condensation
ethyl galactopyranoside
trifluoromethanesulfonic acid
propylene
benzyl glucopyranoside
N-iodosuccinimide
vacciniin

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 journalArticle

Yoshida, Masahiro ; Kiyoi, Takao ; Tsukida, Takahiro ; Kondo, Hirosato. / One-pot synthesis of Lewis X oligosaccharide derivatives using "armed-disarmed" coupling method. In: Journal of Carbohydrate Chemistry. 1998 ; Vol. 17, No. 4-5. pp. 673-681.
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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.",
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