Synthesis of a conformationally locked version of puromycin amino nucleoside

Yongseok Choi; Clifford George; Peter Strazewski; Victor E. Marquez

doi:10.1021/ol010288c

Synthesis of a conformationally locked version of puromycin amino nucleoside

Yongseok Choi, Clifford George, Peter Strazewski, Victor E. Marquez

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

24 Citations (Scopus)

Abstract

(formula presented) A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6-chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3′ (nucleoside numbering) involving a nucleophilic displacement with azide.

Original language	English
Pages (from-to)	589-592
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	4
DOIs	https://doi.org/10.1021/ol010288c
Publication status	Published - 2002 Feb 21
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol010288c

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title = "Synthesis of a conformationally locked version of puromycin amino nucleoside",

abstract = "(formula presented) A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6-chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3′ (nucleoside numbering) involving a nucleophilic displacement with azide.",

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T1 - Synthesis of a conformationally locked version of puromycin amino nucleoside

AU - Choi, Yongseok

AU - George, Clifford

AU - Strazewski, Peter

AU - Marquez, Victor E.

PY - 2002/2/21

Y1 - 2002/2/21

N2 - (formula presented) A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6-chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3′ (nucleoside numbering) involving a nucleophilic displacement with azide.

AB - (formula presented) A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6-chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3′ (nucleoside numbering) involving a nucleophilic displacement with azide.

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JO - Organic Letters

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Synthesis of a conformationally locked version of puromycin amino nucleoside

Abstract

ASJC Scopus subject areas

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