Syntheses of 1,5-dideoxy-1,5-imino-D-mannitol from D-mannose and from D-glucose

G. W.J. Fleet, M. J. Gough, Tony Kung Ming Shing

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Unambiguous enantiospecific syntheses of 1,5-dideoxy-1,5-imino-D-mannitol (LU1, 1-deoxy-mannojirimycin) are reported (i) from D-mannose via hydrogenation of a 5-azido-5-deoxy mannose, and (ii) from D-glucose, in which the key step involves nucleophilic substitution of a trifluoromethanesulphonyl group from C-2 of D-glucose.

Original languageEnglish
Pages (from-to)4029-4032
Number of pages4
JournalTetrahedron Letters
Volume25
Issue number36
DOIs
Publication statusPublished - 1984 Jan 1
Externally publishedYes

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1-Deoxynojirimycin
Mannose
Glucose
Hydrogenation
Substitution reactions

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Syntheses of 1,5-dideoxy-1,5-imino-D-mannitol from D-mannose and from D-glucose. / Fleet, G. W.J.; Gough, M. J.; Shing, Tony Kung Ming.

In: Tetrahedron Letters, Vol. 25, No. 36, 01.01.1984, p. 4029-4032.

Research output: Contribution to journalArticle

Fleet, G. W.J. ; Gough, M. J. ; Shing, Tony Kung Ming. / Syntheses of 1,5-dideoxy-1,5-imino-D-mannitol from D-mannose and from D-glucose. In: Tetrahedron Letters. 1984 ; Vol. 25, No. 36. pp. 4029-4032.
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