Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol, a glucosidase inhibitor

Janos Kuszmann, L. Kiss

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

1,2:5,6-Di-O-isopropylidene-d-glucitol was converted via its 1,4-dimethanesulfonate into the 1-azido-4-methanesulfonate which, after deprotection and treatment with barium hydroxide, afforded a 9:1 mixture of the corresponding 3,4- and 4,5-anhydro derivatives. Reduction of this mixture by transfer hydrogenation using ammonium formate in methanol and Pd/C as catalyst afforded 1,4-dideoxy-1,4-imino-d-glucitol (4), the structure of which was proved after acetylation by 1H-n.m.r. spectroscopy. Compound 4 is a potent α-d-glucosidase inhibitor (Ki 7 × 10-4m) and a less potent β-d-glucosidase inhibitor (Ki 1.25 × 10-4m), and inhibits β-d-galactosidase non-competitively.

Original languageEnglish
Pages (from-to)45-53
Number of pages9
JournalCarbohydrate Research
Volume153
Issue number1
DOIs
Publication statusPublished - Sep 15 1986

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Glucosidases
formic acid
Sorbitol
Galactosidases
Acetylation
Hydrogenation
Methanol
Spectrum Analysis
Spectroscopy
Derivatives
Catalysts
methanesulfonic acid
propylene
barium hydroxide

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol, a glucosidase inhibitor. / Kuszmann, Janos; Kiss, L.

In: Carbohydrate Research, Vol. 153, No. 1, 15.09.1986, p. 45-53.

Research output: Contribution to journalArticle

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N2 - 1,2:5,6-Di-O-isopropylidene-d-glucitol was converted via its 1,4-dimethanesulfonate into the 1-azido-4-methanesulfonate which, after deprotection and treatment with barium hydroxide, afforded a 9:1 mixture of the corresponding 3,4- and 4,5-anhydro derivatives. Reduction of this mixture by transfer hydrogenation using ammonium formate in methanol and Pd/C as catalyst afforded 1,4-dideoxy-1,4-imino-d-glucitol (4), the structure of which was proved after acetylation by 1H-n.m.r. spectroscopy. Compound 4 is a potent α-d-glucosidase inhibitor (Ki 7 × 10-4m) and a less potent β-d-glucosidase inhibitor (Ki 1.25 × 10-4m), and inhibits β-d-galactosidase non-competitively.

AB - 1,2:5,6-Di-O-isopropylidene-d-glucitol was converted via its 1,4-dimethanesulfonate into the 1-azido-4-methanesulfonate which, after deprotection and treatment with barium hydroxide, afforded a 9:1 mixture of the corresponding 3,4- and 4,5-anhydro derivatives. Reduction of this mixture by transfer hydrogenation using ammonium formate in methanol and Pd/C as catalyst afforded 1,4-dideoxy-1,4-imino-d-glucitol (4), the structure of which was proved after acetylation by 1H-n.m.r. spectroscopy. Compound 4 is a potent α-d-glucosidase inhibitor (Ki 7 × 10-4m) and a less potent β-d-glucosidase inhibitor (Ki 1.25 × 10-4m), and inhibits β-d-galactosidase non-competitively.

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