N-glycosylation of 2,3-dideoxyfuranose derivatives having difluoromethylene-phosphonate and -phosphonothioate functionality at the 3 alpha-position

TiCl4- Mediated N-glycosylation of 2,3-dideoxyribofunanosides having a difluoromethylene-phosphonate or -phosphonothioate functional group at the 3alpha-position with silylated pyrimidines was examined. The phosphonate functional was a good directing group to induce alpha-N-glycosylation for alpha-N...

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Bibliographic Details
Published inSynlett no. 10; pp. 1657 - 1660
Main Authors Murano, T, Muroyama, S, Yokomatsu, T, Shibuya, S
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID-DERIVATIVES
3-POSITION
neighbouring-group effects
PYRIMIDINE
PHOSPHATES
CHEMISTRY
nucleotide analogues
MULTISUBSTRATE ANALOG INHIBITORS
N-glycosylations
phosphorus
fluorine
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Summary:TiCl4- Mediated N-glycosylation of 2,3-dideoxyribofunanosides having a difluoromethylene-phosphonate or -phosphonothioate functional group at the 3alpha-position with silylated pyrimidines was examined. The phosphonate functional was a good directing group to induce alpha-N-glycosylation for alpha-N-3-pyrimidine-nucleotide analogue 13 in high diastereoselectivity. The phosphonothioate was an effective functional group to give beta-N-1-pyrimidine-nucleotide analogues 18a-c with good diastereoselectivity. The nucleotide analogue 18a was transformed to the difluoromethylenephosphonate analogue 20 of thymidine-3'-phosphate by oxidation with MCPBA, followed by aqueous work-up.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2002-34218