Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism

Hirosato Kondo, Shin Aoki, Yoshitaka Ichikawa, Randall L. Halcomb, Helena Ritzen, Chi Huey Wong

Research output: Contribution to journalArticle

117 Citations (Scopus)

Abstract

The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and acceptors for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.

Original languageEnglish
Pages (from-to)864-877
Number of pages14
JournalJournal of Organic Chemistry
Volume59
Issue number4
DOIs
Publication statusPublished - Feb 1 1994
Externally publishedYes

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Phosphites
Glycosylation
Glycosides
Glycopeptides
Substrates

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Kondo, H., Aoki, S., Ichikawa, Y., Halcomb, R. L., Ritzen, H., & Wong, C. H. (1994). Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism. Journal of Organic Chemistry, 59(4), 864-877. https://doi.org/10.1021/jo00083a032

Glycosyl Phosphites as Glycosylation Reagents : Scope and Mechanism. / Kondo, Hirosato; Aoki, Shin; Ichikawa, Yoshitaka; Halcomb, Randall L.; Ritzen, Helena; Wong, Chi Huey.

In: Journal of Organic Chemistry, Vol. 59, No. 4, 01.02.1994, p. 864-877.

Research output: Contribution to journalArticle

Kondo, H, Aoki, S, Ichikawa, Y, Halcomb, RL, Ritzen, H & Wong, CH 1994, 'Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism', Journal of Organic Chemistry, vol. 59, no. 4, pp. 864-877. https://doi.org/10.1021/jo00083a032
Kondo, Hirosato ; Aoki, Shin ; Ichikawa, Yoshitaka ; Halcomb, Randall L. ; Ritzen, Helena ; Wong, Chi Huey. / Glycosyl Phosphites as Glycosylation Reagents : Scope and Mechanism. In: Journal of Organic Chemistry. 1994 ; Vol. 59, No. 4. pp. 864-877.
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