De Novo highly stereocontrolled synthesis of 2,6-dideoxy-C-3-branched carbohydrates by use of 2,6-anhydro-2-thio sugar: l-cladinose and its C-3 epimer

Kazunobu Toshima, Takehito Yoshida, Satsuki Mukaiyama, Kuniaki Tatsuta

Research output: Contribution to journal › Article

8 Citations (Scopus)

Abstract

L-Cladinose (1) and its C-3 epimer 2 were synthesized through a highly stereoselective addition of methyl anion to the C-3 carbonyl groups of α-anomer 9 and β-anomer 10 having 2,6-anhydro-2-thio structures, respectively, which were prepared from the common intermediate 6 in stereocontrolled fashion.

Original languageEnglish
Pages (from-to)4139-4142
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number33
DOIs
Publication statusPublished - 1991 Aug 12

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Thiosugars
Anions
Carbohydrates
cladinose

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

De Novo highly stereocontrolled synthesis of 2,6-dideoxy-C-3-branched carbohydrates by use of 2,6-anhydro-2-thio sugar : l-cladinose and its C-3 epimer. / Toshima, Kazunobu; Yoshida, Takehito; Mukaiyama, Satsuki; Tatsuta, Kuniaki.

In: Tetrahedron Letters, Vol. 32, No. 33, 12.08.1991, p. 4139-4142.

Research output: Contribution to journal › Article

Toshima, K, Yoshida, T, Mukaiyama, S & Tatsuta, K 1991, 'De Novo highly stereocontrolled synthesis of 2,6-dideoxy-C-3-branched carbohydrates by use of 2,6-anhydro-2-thio sugar: l-cladinose and its C-3 epimer', Tetrahedron Letters, vol. 32, no. 33, pp. 4139-4142. https://doi.org/10.1016/S0040-4039(00)79886-8
Toshima K, Yoshida T, Mukaiyama S, Tatsuta K. De Novo highly stereocontrolled synthesis of 2,6-dideoxy-C-3-branched carbohydrates by use of 2,6-anhydro-2-thio sugar: l-cladinose and its C-3 epimer. Tetrahedron Letters. 1991 Aug 12;32(33):4139-4142. https://doi.org/10.1016/S0040-4039(00)79886-8
Toshima, Kazunobu ; Yoshida, Takehito ; Mukaiyama, Satsuki ; Tatsuta, Kuniaki. / De Novo highly stereocontrolled synthesis of 2,6-dideoxy-C-3-branched carbohydrates by use of 2,6-anhydro-2-thio sugar : l-cladinose and its C-3 epimer. In: Tetrahedron Letters. 1991 ; Vol. 32, No. 33. pp. 4139-4142.
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