Nucleosides. CXLIV. Some reactions of 2-0-triflyl-2,3’-anhydroxylosyluracil with nucleophilic reagents. Synthesis of 2‘-chloro-2’,3’-dideoxyuridinene. Studies directed toward the synthesis of 2‘-deoxy-2’-substituted arabino nucleosides. (5) Journal Article

  

Authors:	Pankiewicz, K. W.; Watanabe, K. A.
Article Title:	Nucleosides. CXLIV. Some reactions of 2-0-triflyl-2,3’-anhydroxylosyluracil with nucleophilic reagents. Synthesis of 2‘-chloro-2’,3’-dideoxyuridinene. Studies directed toward the synthesis of 2‘-deoxy-2’-substituted arabino nucleosides. (5)
Abstract:	Treatment of ‘-anhydro-4-(5-0-acety1-2-0-triflyl-fl-D-xylofuranosyl)uracil β-D-xylofuranosyluracil with LiCl in hexamethylphosphoric triamide afforded the 2’-“up” chloride of the anhydronucleoside, i.e. 2’-triflate group was directly displaced by the chloride nucleophile. All attempts to hydrolyze the 2,3’-anhydro linkage resulted in the formation of 2’-chloro-2’,3’-didehydro-dideoxynucleoside. © 1987, The Pharmaceutical Society of Japan. All rights reserved.
Keywords:	unclassified drug; nonhuman; methodology; chemistry; arabinonucleosides; deoxyuridine; support, u.s. gov't, p.h.s.; drug analysis; 3-didehydro-2; 3-dideoxy-β ~; 3’-anhydro-l-(2-0- triflyl-β; 3’-anhydro-l-(2-chloro-2-deoxy-β; 3’-dideoxyuridinene; d-glyceropento-2-enofuranosyl)uracil 2’-chloro-2’; d-lyxofuranosyl)uracil l-(2-chloro-2; d-xylofuranosyl)uracil 2; nucleoside anhydronucleoside reaction mechanism 2; 2,3' anhydrouracil derivative
Journal Title:	Chemical and Pharmaceutical Bulletin
Volume:	35
Issue:	11
ISSN:	0009-2363
Publisher:	Pharmaceutical Society of Japan
Date Published:	1987-11-25
Start Page:	4498
End Page:	4502
Language:	English
DOI:	10.1248/cpb.35.4498
PUBMED:	3442884
PROVIDER:	scopus
DOI/URL:	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0023521188&doi=10.1248%2fcpb.35.4498&partnerID=40&md5=4e4e8d350126dad63dc619e47b155910
Notes:	Article -- Export Date: 5 February 2021 -- Source: Scopus

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