De novo highly stereocontrolled synthesis of 2,6-dideoxy sugars by use of 2,6-anhydro-2-thio sugars

Kazunobu Toshima, Takehito Yoshida, Satsuki Mukaiyama, Kuniaki Tatsuta

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Representative 2,6-dideoxy sugars, l-cladinose (1), l-mycarose (2), l-oleandrose (3), l-olivose (4), and all of their C-3 epimers, 2,6-dideoxy-3-C-methyl-3-O-methyl-l-arabino-hexopyranose (26), 2,6-dideoxy-3-C-methyl-l-arabino-hexopyranose (l-olivomycose) (27), 2,6-dideoxy-3-O-methyl-l-ribo-hexopyranose (l-cymarose) (32), and 2,6-dideoxy-l-ribo-hexopyranose (l-digitoxose) (33) have been stereospecifically synthesized through a highly stereoselective addition of a nucleophilic reagent to the C-3 carbonyl groups of methyl 2,6-anhydro-4-O-benzyl-2-thio-α-l-arabino-hexopyranosid-3-ulose (11) or methyl 2,6-anhydro-4-O-benzyl-2-thio-β-l-arabino-hexopyranosid-3-ulose (12) possessing 2,6-anhydro-2-thio structures. Anomers 11 and 12 were both prepared in stereocontrolled fashion by treatment of a common intermediate, methyl 2,6-anhydro-4-O-benzyl-3-O-tetrahydropyranyl-2-thio-α-l-altropyranoside (8) with Lewis acids in methanol followed by oxidation.

Original languageEnglish
Pages (from-to)173-188
Number of pages16
JournalCarbohydrate Research
Volume222
Issue numberC
DOIs
Publication statusPublished - 1991 Dec 30

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Thiosugars
Lewis Acids
Sugars
Methanol
Oxidation
oleandrose
mycarose
olivose
digitoxose
cladinose

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

De novo highly stereocontrolled synthesis of 2,6-dideoxy sugars by use of 2,6-anhydro-2-thio sugars. / Toshima, Kazunobu; Yoshida, Takehito; Mukaiyama, Satsuki; Tatsuta, Kuniaki.

In: Carbohydrate Research, Vol. 222, No. C, 30.12.1991, p. 173-188.

Research output: Contribution to journalArticle

Toshima, Kazunobu ; Yoshida, Takehito ; Mukaiyama, Satsuki ; Tatsuta, Kuniaki. / De novo highly stereocontrolled synthesis of 2,6-dideoxy sugars by use of 2,6-anhydro-2-thio sugars. In: Carbohydrate Research. 1991 ; Vol. 222, No. C. pp. 173-188.
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abstract = "Representative 2,6-dideoxy sugars, l-cladinose (1), l-mycarose (2), l-oleandrose (3), l-olivose (4), and all of their C-3 epimers, 2,6-dideoxy-3-C-methyl-3-O-methyl-l-arabino-hexopyranose (26), 2,6-dideoxy-3-C-methyl-l-arabino-hexopyranose (l-olivomycose) (27), 2,6-dideoxy-3-O-methyl-l-ribo-hexopyranose (l-cymarose) (32), and 2,6-dideoxy-l-ribo-hexopyranose (l-digitoxose) (33) have been stereospecifically synthesized through a highly stereoselective addition of a nucleophilic reagent to the C-3 carbonyl groups of methyl 2,6-anhydro-4-O-benzyl-2-thio-α-l-arabino-hexopyranosid-3-ulose (11) or methyl 2,6-anhydro-4-O-benzyl-2-thio-β-l-arabino-hexopyranosid-3-ulose (12) possessing 2,6-anhydro-2-thio structures. Anomers 11 and 12 were both prepared in stereocontrolled fashion by treatment of a common intermediate, methyl 2,6-anhydro-4-O-benzyl-3-O-tetrahydropyranyl-2-thio-α-l-altropyranoside (8) with Lewis acids in methanol followed by oxidation.",
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