Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-d-glucopyranoside

Yoko Akashi, Kenichi Takao, Kin ichi Tadano

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Allylation and benzylation at the α-carbon of α-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside provided the respective α,α-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate.

Original languageEnglish
Pages (from-to)1139-1142
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number10
DOIs
Publication statusPublished - 2009 Mar 11

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Alkylation
Carbon
Allylation
Stereochemistry
Derivatives
Substrates

Keywords

  • α-Alkylation
  • Asymmetric synthesis
  • Carbohydrates
  • Chiral auxiliary
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-d-glucopyranoside. / Akashi, Yoko; Takao, Kenichi; Tadano, Kin ichi.

In: Tetrahedron Letters, Vol. 50, No. 10, 11.03.2009, p. 1139-1142.

Research output: Contribution to journalArticle

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abstract = "Allylation and benzylation at the α-carbon of α-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside provided the respective α,α-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate.",
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T1 - Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-d-glucopyranoside

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AU - Takao, Kenichi

AU - Tadano, Kin ichi

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N2 - Allylation and benzylation at the α-carbon of α-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside provided the respective α,α-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate.

AB - Allylation and benzylation at the α-carbon of α-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside provided the respective α,α-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate.

KW - α-Alkylation

KW - Asymmetric synthesis

KW - Carbohydrates

KW - Chiral auxiliary

KW - Stereoselective synthesis

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