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Facile synthesis of 4-deoxy-4-fluoro-alpha-D-talopyranoside, 4-deoxy-4-fluoro-alpha-D-idopyranoside and 2,4-dideoxy-2,4-difluoro-alpha-D-talopyranoside

Abstract:

The title compounds were prepared by two independent syntheses using inexpensive commercially available starting materials. 4-Deoxy-4-fluoro-α- d-talopyranoside served as a precursor to 4-deoxy-4-fluoro-α-d- idopyranoside, allowing for inversion of configuration at C-3 via a three-step protocol. The synthesis of 2,4-dideoxy-2,4-difluoro-α-d-talopyranoside is based on two nucleophilic fluorination events at C-2 then at C-4 using TBAF·3H2O and TBAF·4tBuOH as a fluoride source. All compounds are...

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Publication status:
Published

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
JOURNAL OF FLUORINE CHEMISTRY More from this journal
Volume:
132
Issue:
10
Pages:
772-778
Publication date:
2011-10-01
DOI:
ISSN:
0022-1139
Language:
English
Keywords:
Pubs id:
pubs:186261
UUID:
uuid:0c8d9c8c-0f56-4286-9535-144173490f34
Local pid:
pubs:186261
Source identifiers:
186261
Deposit date:
2012-12-19

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