TY - JOUR
T1 - 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)
AU - Pankiewicz, Krzysztof W.
AU - Watanabea, Kyoichi A.
PY - 1987
Y1 - 1987
N2 - 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.
AB - 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.
KW - 3-didehydro-2
KW - 3-dideoxy-β ~
KW - 3’-anhydro-l-(2-0- triflyl-β
KW - 3’-anhydro-l-(2-chloro-2-deoxy-β
KW - 3’-dideoxyuridinene
KW - D-glyceropento-2-enofuranosyl)uracil 2’-chloro-2’
KW - D-lyxofuranosyl)uracil l-(2-chloro-2
KW - D-xylofuranosyl)uracil 2
KW - nucleoside anhydronucleoside reaction mechanism 2
UR - http://www.scopus.com/inward/record.url?scp=0023521188&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0023521188&partnerID=8YFLogxK
U2 - 10.1248/cpb.35.4498
DO - 10.1248/cpb.35.4498
M3 - Article
C2 - 3442884
AN - SCOPUS:0023521188
SN - 0009-2363
VL - 35
SP - 4498
EP - 4502
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 11
ER -