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

doi:10.1016/S0040-4039(00)79886-8

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	4139-4142
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)79886-8
Publication status	Published - 1991 Aug 12

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "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",

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.",

author = "Kazunobu Toshima and Takehito Yoshida and Satsuki Mukaiyama and Kuniaki Tatsuta",

year = "1991",

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language = "English",

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pages = "4139--4142",

journal = "Tetrahedron Letters",

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T1 - De Novo highly stereocontrolled synthesis of 2,6-dideoxy-C-3-branched carbohydrates by use of 2,6-anhydro-2-thio sugar

T2 - l-cladinose and its C-3 epimer

AU - Toshima, Kazunobu

AU - Yoshida, Takehito

AU - Mukaiyama, Satsuki

AU - Tatsuta, Kuniaki

PY - 1991/8/12

Y1 - 1991/8/12

N2 - 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.

AB - 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.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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