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5'-Halogeno-2',3'-cyclic sulphite isomers in the preparation of 5'-halogeno nucleosides. Synthesis of 5'-deoxyuridine and 5'-deoxy-5-fluorouridine.
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MedLine Citation:
PMID:  148036     Owner:  NLM     Status:  MEDLINE    
When uridine (Ia) is reacted with thionyl chloride in hexamethylphosphoric triamide a mixture of isomeric 5'-chloro-2',3'-sulphites is formed, which can be separated to individual epimers IIa and IIIa, in 45% and 15% yields, respectively. Analogously, crystalline epimers IIb (37%) and IIIb (17%) can be obtained from 5-fluorouridine (Ib). Both isomers IIa, IIIa (or IIb, IIIb) afford a single 5'-chloro derivative IVa (or IVb, respectively) if treated with 0.1N sodium methoxide. From the mixture of sulphites IIa and IIIa (or IIb and IIIb) crystalline 5'-chlorouridine IVa is formed in 84.5% yield, calculated per starting uridine Ia (or crystalline 5'-chloro-5-fluorouridine IVb, 85.5% per starting 5-fluorouridine Ib, respectively). On reduction of 5'-chlorouridine IVa with tributyltin hydride 5'-deoxyuridine (Va) is formed in 79% yield. During the reduction of 5'-chloro-5-fluoro derivative IVb to 5'-deoxy-5-fluorouridine (Vb, 57%) a partial reductive elimination of 5-fluorine takes place under formation of 5'-deoxyuridine (Va, 9%).
H Hrebabecký; J Beránek
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Nucleic acids research     Volume:  5     ISSN:  0305-1048     ISO Abbreviation:  Nucleic Acids Res.     Publication Date:  1978 Mar 
Date Detail:
Created Date:  1978-06-12     Completed Date:  1978-06-12     Revised Date:  2009-11-18    
Medline Journal Info:
Nlm Unique ID:  0411011     Medline TA:  Nucleic Acids Res     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  1029-39     Citation Subset:  IM    
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MeSH Terms
Deoxyuridine / chemical synthesis*
Floxuridine / chemical synthesis*
Uridine / analogs & derivatives
Reg. No./Substance:
50-91-9/Floxuridine; 58-96-8/Uridine; 951-78-0/Deoxyuridine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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Journal Information
Journal ID (nlm-ta): Nucleic Acids Res
ISSN: 0305-1048
ISSN: 1362-4962
Article Information
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Print publication date: Month: 3 Year: 1978
Volume: 5 Issue: 3
First Page: 1029 Last Page: 1039
ID: 342042
PubMed Id: 148036

5'-Halogeno-2',3'-cyclic sulphite isomers in the preparation of 5'-halogeno nucleosides. Synthesis of 5'-deoxyuridine and 5'-deoxy-5-fluorouridine.
H Hrebabeck?
J Ber?nek

Article Categories:
  • Research Article

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