The fate of the methanesulfonyloxy group on reduction with LAH

Éva Bozó, Sándor Boros, János Kuszmann, E. Gács-Baitz

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Reduction of 1,6:2,5-dianhydro-3,4-di-O-methanesulfonyl-1-thio-D- glucitol with LAH afforded the corresponding 3,4-dihydroxy compound in a yield of 51% and six by-products were isolated after acetylation. Three differed from the original molecule only in the substituents, which were AcO at C-3 and H, CH3S and CH3SCH2S at C-4, respectively. The other compounds had a rearranged skeleton and were 1,4:2,5-dianhydro-1-thio-D-galactitol derivatives, containing the AcO group at C-3 and the aforementioned three substituents attached to C-6. A mechanism is suggested for the rearrangement, and for the formation of the substituents including the fate of the methanesulfonyloxy groups on reduction with LAH which is generally applicable to any mesyloxy derivative.

Original languageEnglish
Pages (from-to)8095-8102
Number of pages8
JournalTetrahedron
Volume55
Issue number26
DOIs
Publication statusPublished - Jun 25 1999

Fingerprint

Galactitol
Sorbitol
Acetylation
Skeleton
Derivatives
Byproducts
Molecules

Keywords

  • Mechanisms
  • Rearrangements
  • Reduction
  • Stereochemistry
  • Sulfonic acids and derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The fate of the methanesulfonyloxy group on reduction with LAH. / Bozó, Éva; Boros, Sándor; Kuszmann, János; Gács-Baitz, E.

In: Tetrahedron, Vol. 55, No. 26, 25.06.1999, p. 8095-8102.

Research output: Contribution to journalArticle

Bozó, Éva ; Boros, Sándor ; Kuszmann, János ; Gács-Baitz, E. / The fate of the methanesulfonyloxy group on reduction with LAH. In: Tetrahedron. 1999 ; Vol. 55, No. 26. pp. 8095-8102.
@article{f42d3b9b52ad4a758083493b1e0c81dc,
title = "The fate of the methanesulfonyloxy group on reduction with LAH",
abstract = "Reduction of 1,6:2,5-dianhydro-3,4-di-O-methanesulfonyl-1-thio-D- glucitol with LAH afforded the corresponding 3,4-dihydroxy compound in a yield of 51{\%} and six by-products were isolated after acetylation. Three differed from the original molecule only in the substituents, which were AcO at C-3 and H, CH3S and CH3SCH2S at C-4, respectively. The other compounds had a rearranged skeleton and were 1,4:2,5-dianhydro-1-thio-D-galactitol derivatives, containing the AcO group at C-3 and the aforementioned three substituents attached to C-6. A mechanism is suggested for the rearrangement, and for the formation of the substituents including the fate of the methanesulfonyloxy groups on reduction with LAH which is generally applicable to any mesyloxy derivative.",
keywords = "Mechanisms, Rearrangements, Reduction, Stereochemistry, Sulfonic acids and derivatives",
author = "{\'E}va Boz{\'o} and S{\'a}ndor Boros and J{\'a}nos Kuszmann and E. G{\'a}cs-Baitz",
year = "1999",
month = "6",
day = "25",
doi = "10.1016/S0040-4020(99)00417-2",
language = "English",
volume = "55",
pages = "8095--8102",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "26",

}

TY - JOUR

T1 - The fate of the methanesulfonyloxy group on reduction with LAH

AU - Bozó, Éva

AU - Boros, Sándor

AU - Kuszmann, János

AU - Gács-Baitz, E.

PY - 1999/6/25

Y1 - 1999/6/25

N2 - Reduction of 1,6:2,5-dianhydro-3,4-di-O-methanesulfonyl-1-thio-D- glucitol with LAH afforded the corresponding 3,4-dihydroxy compound in a yield of 51% and six by-products were isolated after acetylation. Three differed from the original molecule only in the substituents, which were AcO at C-3 and H, CH3S and CH3SCH2S at C-4, respectively. The other compounds had a rearranged skeleton and were 1,4:2,5-dianhydro-1-thio-D-galactitol derivatives, containing the AcO group at C-3 and the aforementioned three substituents attached to C-6. A mechanism is suggested for the rearrangement, and for the formation of the substituents including the fate of the methanesulfonyloxy groups on reduction with LAH which is generally applicable to any mesyloxy derivative.

AB - Reduction of 1,6:2,5-dianhydro-3,4-di-O-methanesulfonyl-1-thio-D- glucitol with LAH afforded the corresponding 3,4-dihydroxy compound in a yield of 51% and six by-products were isolated after acetylation. Three differed from the original molecule only in the substituents, which were AcO at C-3 and H, CH3S and CH3SCH2S at C-4, respectively. The other compounds had a rearranged skeleton and were 1,4:2,5-dianhydro-1-thio-D-galactitol derivatives, containing the AcO group at C-3 and the aforementioned three substituents attached to C-6. A mechanism is suggested for the rearrangement, and for the formation of the substituents including the fate of the methanesulfonyloxy groups on reduction with LAH which is generally applicable to any mesyloxy derivative.

KW - Mechanisms

KW - Rearrangements

KW - Reduction

KW - Stereochemistry

KW - Sulfonic acids and derivatives

UR - http://www.scopus.com/inward/record.url?scp=0033603634&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033603634&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(99)00417-2

DO - 10.1016/S0040-4020(99)00417-2

M3 - Article

AN - SCOPUS:0033603634

VL - 55

SP - 8095

EP - 8102

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 26

ER -