Synthesis of new sugar derivatives having potential antitumour activity. Part XVII. Synthesis and oxidation of 1,4

3,6-bis(thioanhydro)-D-iditol and its 2,5-diacetate

J. Kuszmann, P. Sohár

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The synthesis of 1,4:3,6-bis(thioanhydro)-D-iditol (7) and its 2,5-diacetate (9), starting from 3,4-di-O-methylsulfonyl-D-mannitol is described. Oxidation of 7 led to the corresponding disulfone 10; no sulfoxide could be separated. The diacetate 9 gave on oxidation two isomeric (R,R)- and (R,S)-disulfoxides (12 and 14), a sulfone-sulfoxide (17), and the disulfone (11). Structures were proved by spectroscopic methods.

Original languageEnglish
Pages (from-to)19-27
Number of pages9
JournalCarbohydrate Research
Volume21
Issue number1
DOIs
Publication statusPublished - 1972

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sulfoxide
Sugars
Thermodynamic properties
Derivatives
Oxidation
Sulfones
Mannitol
1,4-3,6-bis(thioanhydro)-D-iditol

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

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title = "Synthesis of new sugar derivatives having potential antitumour activity. Part XVII. Synthesis and oxidation of 1,4: 3,6-bis(thioanhydro)-D-iditol and its 2,5-diacetate",
abstract = "The synthesis of 1,4:3,6-bis(thioanhydro)-D-iditol (7) and its 2,5-diacetate (9), starting from 3,4-di-O-methylsulfonyl-D-mannitol is described. Oxidation of 7 led to the corresponding disulfone 10; no sulfoxide could be separated. The diacetate 9 gave on oxidation two isomeric (R,R)- and (R,S)-disulfoxides (12 and 14), a sulfone-sulfoxide (17), and the disulfone (11). Structures were proved by spectroscopic methods.",
author = "J. Kuszmann and P. Soh{\'a}r",
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journal = "Carbohydrate Research",
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T1 - Synthesis of new sugar derivatives having potential antitumour activity. Part XVII. Synthesis and oxidation of 1,4

T2 - 3,6-bis(thioanhydro)-D-iditol and its 2,5-diacetate

AU - Kuszmann, J.

AU - Sohár, P.

PY - 1972

Y1 - 1972

N2 - The synthesis of 1,4:3,6-bis(thioanhydro)-D-iditol (7) and its 2,5-diacetate (9), starting from 3,4-di-O-methylsulfonyl-D-mannitol is described. Oxidation of 7 led to the corresponding disulfone 10; no sulfoxide could be separated. The diacetate 9 gave on oxidation two isomeric (R,R)- and (R,S)-disulfoxides (12 and 14), a sulfone-sulfoxide (17), and the disulfone (11). Structures were proved by spectroscopic methods.

AB - The synthesis of 1,4:3,6-bis(thioanhydro)-D-iditol (7) and its 2,5-diacetate (9), starting from 3,4-di-O-methylsulfonyl-D-mannitol is described. Oxidation of 7 led to the corresponding disulfone 10; no sulfoxide could be separated. The diacetate 9 gave on oxidation two isomeric (R,R)- and (R,S)-disulfoxides (12 and 14), a sulfone-sulfoxide (17), and the disulfone (11). Structures were proved by spectroscopic methods.

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SN - 0008-6215

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