| Nucleic acid related compounds. 118. Nonaqueous diazotization of aminopurine derivatives. Convenient access to 6-halo- and 2,6-dihalopurine nucleosides and 2'-deoxynucleosides with acyl or silyl halides. | |
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MedLine Citation:
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PMID: 12530909 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Treatment of 9-(2,3,5-tri-O-acetyl-beta-d-ribofuranosyl)-2-amino-6-chloropurine (1) with TMS-Cl and benzyltriethylammonium nitrite (BTEA-NO2) in dichloromethane gave the crystalline 2,6-dichloropurine nucleoside 2, and acetyl chloride/BTEA-NO2 was equally effective ( approximately 85%, without chromatography). TMS-Br/tert-butyl nitrite/dibromomethane gave crystalline 2-bromo-6-chloro analogue 3 (85%). (Chloro or bromo)-dediazoniation of 3',5'-di-O-acetyl-2'-deoxyadenosine (4) gave the 6-[chloro (5, 63%) or bromo (6, 80%)]purine deoxynucleosides, and 2',3',5'-tri-O-acetyladenosine (8) was converted into the 6-chloropurine nucleoside 9 (71%). |
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Authors:
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Paula Francom; Morris J Robins |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 68 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2003 Jan |
Date Detail:
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Created Date: 2003-01-17 Completed Date: 2003-07-07 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 666-9 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Chromatography, Thin Layer Indicators and Reagents Magnetic Resonance Spectroscopy Molecular Structure Nucleic Acids / chemistry* Purine Nucleosides / analysis, chemical synthesis*, chemistry* |
| Chemical | |
Reg. No./Substance:
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0/9-(2,3,5-tri-O-acetylribofuranosyl)-2-amino-6-chloropurine; 0/Indicators and Reagents; 0/Nucleic Acids; 0/Purine Nucleosides |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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