A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside

S. Todd Deal; Derek Horton

doi:10.1016/S0008-6215(98)00325-5

A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside

S. Todd Deal, Derek Horton

Emeriti, Retired & In Memoriam (CBSS)

Ohio State University

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

3 Scopus citations

Abstract

The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-α-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. Copyright (C) 1999 Elsevier Science Ltd.

Original language	English
Pages (from-to)	187-191
Number of pages	5
Journal	Carbohydrate Research
Volume	315
Issue number	1-2
DOIs	https://doi.org/10.1016/S0008-6215(98)00325-5
State	Published - Jan 31 1999

Scopus Subject Areas

Analytical Chemistry
Biochemistry
Organic Chemistry

Keywords

2,6-Dideoxy-2-fluoro-L-talose
Anthracycline glycons
Configurational inversion
Fluoro sugars

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10.1016/S0008-6215(98)00325-5

Cite this

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title = "A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside",

abstract = "The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-α-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. Copyright (C) 1999 Elsevier Science Ltd.",

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doi = "10.1016/S0008-6215(98)00325-5",

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T1 - A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside

AU - Deal, S. Todd

AU - Horton, Derek

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N2 - The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-α-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. Copyright (C) 1999 Elsevier Science Ltd.

AB - The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-α-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. Copyright (C) 1999 Elsevier Science Ltd.

KW - 2,6-Dideoxy-2-fluoro-L-talose

KW - Anthracycline glycons

KW - Configurational inversion

KW - Fluoro sugars

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DO - 10.1016/S0008-6215(98)00325-5

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A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside

Abstract

Scopus Subject Areas

Keywords

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