A new route for preparation of 5-deoxy-5-hydroxyphosphinyl-D-gluco- and L-idopyranose derivatives

Tadashi Hanaya, Yasushi Fujii, Satoru Ikejiri, Hiroshi Yamamoto

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

By starting with known 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo- hexofuranos-5-ulose (5), the 3,6-di-O-benzyl derivatives (8 and 10) of the title phospho-sugar analogs were prepared in six steps through the key intermediates, 5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-gluco- and -L-idofuranoses (7a and 7b), respectively. These products (8 and 10) were respectively converted into the corresponding 1,2,4-tri-O-acetyl-5- methoxyphosphinyl derivatives (9 and 11), whose structures and conformations (mostly in 4C1) were established by spectroscopy.

Original languageEnglish
Pages (from-to)323-332
Number of pages10
JournalHeterocycles
Volume50
Issue number1
DOIs
Publication statusPublished - Jan 1 1999

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Fingerprint Dive into the research topics of 'A new route for preparation of 5-deoxy-5-hydroxyphosphinyl-D-gluco- and L-idopyranose derivatives'. Together they form a unique fingerprint.

Cite this