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)

Krzysztof W. Pankiewicz; Kyoichi A. Watanabea

doi:10.1248/cpb.35.4498

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)

Krzysztof W. Pankiewicz
, Kyoichi A. Watanabea

Center for Drug Design

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

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.

Original language	English (US)
Pages (from-to)	4498-4502
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	35
Issue number	11
DOIs	https://doi.org/10.1248/cpb.35.4498
State	Published - 1987

Keywords

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

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Pankiewicz, K. W., & Watanabea, K. A. (1987). 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). Chemical and Pharmaceutical Bulletin, 35(11), 4498-4502. https://doi.org/10.1248/cpb.35.4498

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). / Pankiewicz, Krzysztof W.; Watanabea, Kyoichi A.
In: Chemical and Pharmaceutical Bulletin, Vol. 35, No. 11, 1987, p. 4498-4502.

Research output: Contribution to journal › Article › peer-review

Pankiewicz, KW & Watanabea, KA 1987, '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)', Chemical and Pharmaceutical Bulletin, vol. 35, no. 11, pp. 4498-4502. https://doi.org/10.1248/cpb.35.4498

Pankiewicz, Krzysztof W. ; Watanabea, Kyoichi A. / 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). In: Chemical and Pharmaceutical Bulletin. 1987 ; Vol. 35, No. 11. pp. 4498-4502.

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abstract = "Treatment of {\textquoteleft}-anhydro-4-(5-0-acety1-2-0-triflyl-fl-D-xylofuranosyl)uracil β-D-xylofuranosyluracil with LiCl in hexamethylphosphoric triamide afforded the 2{\textquoteright}-“up” chloride of the anhydronucleoside, i.e. 2{\textquoteright}-triflate group was directly displaced by the chloride nucleophile. All attempts to hydrolyze the 2,3{\textquoteright}-anhydro linkage resulted in the formation of 2{\textquoteright}-chloro-2{\textquoteright},3{\textquoteright}-didehydro-dideoxynucleoside.",

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AU - Watanabea, Kyoichi A.

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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.

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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

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