Synthesis of 6-deoxy-5-thio-D-glucose

Éva Bozó, Sándor Boros, János Kuszmann, Eszter Gács-Baitz

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Abstract

Three routes were investigated for the conversion of D-glucose into the title compound. In the first approach, reduction of the 5,6-thiirane ring of 5,6-dideoxy-5,6-epithio-1,2-O-isopropylidene-α-D-glucofuranose (17) as well as that of its 3-O-allyl derivative (13) with lithium aluminium hydride was investigated: 17 afforded the corresponding 6-deoxy derivative besides di-, tri-, and polymers, whereas only polymers were formed from 13. In the second approach, the oxirane ring of 3-O-allyl-5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose was reduced by sodium borohydride and the resulting 6-deoxy derivative was converted into the 5-thiobenzoate; the corresponding hex-4-enofuranose was formed as a byproduct. In the third approach partial mesylation of methyl 5-thio-α-D-glucopyranoside was attempted, but the 6-mesylate 27 could be isolated only in modest yield (28%) together with rearranged 2,5-thioanhydromannofuranoside derivatives. The mechanism of this rearrangement is discussed in detail. The 6-mesylate 27 was converted via the 6-iodo derivative into the title compound.

Original languageEnglish
Pages (from-to)159-173
Number of pages15
JournalCarbohydrate Research
Volume290
Issue number2
DOIs
Publication statusPublished - Sep 2 1996

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Keywords

  • 6-deoxy-5-thio-D-glucose
  • reaction mechanism
  • rearrangement reactions of mesylated methyl 5-thio-α-D-glucopyranoside
  • reduction of 5,6-thiirane rings with LiAlH
  • transannular participation of the sulfur atom

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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