A Highly Practical Synthesis of Sulfated Lewis X: One-Pot, Two-Step Glycosylation Using "Armed/Disarmed" Coupling and Selective Benzoylation and Sulfation

Takahiro Tsukida, Masahiro Yoshida, Kiriko Kurokawa, Yoshiyuki Nakai, Toshio Achiha, Takao Kiyoi, Hirosato Kondo

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48 Citations (Scopus)

Abstract

In spite of the several attractive biological activities of the Le x , sLe x , and sulfated Le x derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le x analogs and succeeded in establishing highly practical syntheses of the Le x and sulfated Le x analogs. Especially, the "armed/disarmed" method allowed the first synthesis of Le x derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le x , sulfated Le x , and other derivatives.

Original languageEnglish
Pages (from-to)6876-6881
Number of pages6
JournalJournal of Organic Chemistry
Volume62
Issue number20
DOIs
Publication statusPublished - Jan 1 1997
Externally publishedYes

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Glycosylation
Derivatives
Bioactivity
Oligosaccharides

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

A Highly Practical Synthesis of Sulfated Lewis X : One-Pot, Two-Step Glycosylation Using "Armed/Disarmed" Coupling and Selective Benzoylation and Sulfation. / Tsukida, Takahiro; Yoshida, Masahiro; Kurokawa, Kiriko; Nakai, Yoshiyuki; Achiha, Toshio; Kiyoi, Takao; Kondo, Hirosato.

In: Journal of Organic Chemistry, Vol. 62, No. 20, 01.01.1997, p. 6876-6881.

Research output: Contribution to journalArticle

Tsukida, Takahiro ; Yoshida, Masahiro ; Kurokawa, Kiriko ; Nakai, Yoshiyuki ; Achiha, Toshio ; Kiyoi, Takao ; Kondo, Hirosato. / A Highly Practical Synthesis of Sulfated Lewis X : One-Pot, Two-Step Glycosylation Using "Armed/Disarmed" Coupling and Selective Benzoylation and Sulfation. In: Journal of Organic Chemistry. 1997 ; Vol. 62, No. 20. pp. 6876-6881.
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