A new route for preparation of 5-deoxy-5-(hydroxyphosphinyl)-D-mannopyranose and -L-gulopyranose derivatives

Tadashi Hanaya, Hiroshi Yamamoto

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Starting from methyl 2,3-O-isopropylidene-α-D-mannofuranoside (5), methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose (12) was prepared in three steps. The addition reaction of dimethyl phosphonate to 12, followed by deoxygenation of 5-OH group, provided the 5-deoxy-5-dimethoxyphosphinyl-α-D-mannofuranoside derivative 15a and the β-L-gulofuranoside isomer 15b. Reduction of 15a and 15b with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of HCl and then H2O2, afforded the D-mannopyranose (17) and L-gulopyranose analog 21, each having a phosphinyl group in the hemiacetal ring. These were converted to the corresponding 1,2,3,4,6-penta-O-acetyl-5-methoxyphosphinyl derivatives 19 and 23, respectively, structures and conformations (4C1 or 1C4, resp.) of which were established by 1H-NMR spectroscopy.

Original languageEnglish
Pages (from-to)2608-2618
Number of pages11
JournalHelvetica Chimica Acta
Volume85
Issue number9
DOIs
Publication statusPublished - 2002

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Mannose
routes
deoxygenation
Derivatives
preparation
Rubiaceae
Addition reactions
Isomers
Nuclear magnetic resonance spectroscopy
Conformations
Magnetic Resonance Spectroscopy
isomers
Sodium
sodium
analogs
nuclear magnetic resonance
rings
spectroscopy
propylene
dimethyl hydrogen phosphite

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

A new route for preparation of 5-deoxy-5-(hydroxyphosphinyl)-D-mannopyranose and -L-gulopyranose derivatives. / Hanaya, Tadashi; Yamamoto, Hiroshi.

In: Helvetica Chimica Acta, Vol. 85, No. 9, 2002, p. 2608-2618.

Research output: Contribution to journalArticle

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