An improved synthesis of the 5-deoxy-5-(hydroxyphosphinyl)- d-glucopyranoses, and crystal structures of 1,2,3,4,6-penta-O-acetyl-5-deoxy-5-[(R)-methoxyphosphinyl]- β-d-glucopyranose and its 5-[(R)-ethylphosphinyl] congener

Thomas Richter, Peter Luger, Tadashi Hanaya, Hiroshi Yamamoto

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Treatment of 3-O-acetyl-5-deoxy-5-(dimethoxyphosphinyl)-1,2-O-isopropylidene- α-d-glucofuranose (7) with dihydropyran in the presence of pyridinium p-toluenesulfonate gave the 6-O-(tetrahydropyran-2-yl) derivative in 91% yield. Ring-enlargement of this compound by the known, 2-step procedure gave 5-deoxy- 5-(hydroxyphosphinyl)-d-glucopyranoses in an overall yield from 7 twice as high as that obtained by the previous, alternative route via the corresponding 6-O-(triphenylmethyl)- α-d-glucofuranose precursor. X-Ray crystallographic analyses were performed on the two title compounds, penta-O-acetyl-5-deoxy-5-(methoxyphosphinyl)- (12b) and -5-(ethylphosphinyl)-β-d-glucopyranose (13b). The results show that both have the 4C1 conformation and the substituents on C-1 to C-5 are quasi-equatorial (nomenclature of Jeffrey and Yates). The methoxy group of 12b is in a quasi-equatorial position, whereas the ethyl group of 13b is attached bisectionally to P-5.

Original languageEnglish
Pages (from-to)9-21
Number of pages13
JournalCarbohydrate Research
Volume193
Issue numberC
DOIs
Publication statusPublished - Oct 31 1989

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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