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Titolo:
Photo amidoglycosylation of an allal azidoformate. Synthesis of beta-2-amido allopyranosides
Autore:
Kan, C; Long, CM; Paul, M; Ring, CM; Tully, SE; Rojas, CM;
Indirizzi:
Columbia Univ Barnard Coll, New York, NY 10027 USA Columbia Univ Barnard Coll New York NY USA 10027 , New York, NY 10027 USA
Titolo Testata:
ORGANIC LETTERS
fascicolo: 3, volume: 3, anno: 2001,
pagine: 381 - 384
SICI:
1523-7060(20010208)3:3<381:PAOAAA>2.0.ZU;2-M
Fonte:
ISI
Lingua:
ENG
Soggetto:
VICINAL AMINO-ALCOHOLS; STEREOSELECTIVE SYNTHESIS; GLYCALS; ROUTE; ANALOGS; ETHERS; ACID;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
31
Recensione:
Indirizzi per estratti:
Indirizzo: Rojas, CM Columbia Univ Barnard Coll, 3009 Broadway, New York, NY 10027 USA Columbia Univ Barnard Coll 3009 Broadway New York NY USA 10027 A
Citazione:
C. Kan et al., "Photo amidoglycosylation of an allal azidoformate. Synthesis of beta-2-amido allopyranosides", ORG LETT, 3(3), 2001, pp. 381-384

Abstract

[GRAPHICS]Photolysis of an allal C-3 azidoformate provoked intramolecular nitrene insertion into the glycal C=C unit and allowed direct incorporation of alcohol nucleophiles as a-disposed substituents at C-1, The 5-amido allopyranoside products were elaborated via N-acylation and selective oxazolidinone hydrolysis, providing N-Boc-protected 2-amino sugars and simplifying stereochemical assignments. Synthesis of the potentially labile allal azidoformate was achieved via reaction of the corresponding carbonyl imidazolide with trimethylsilyl azide, facilitated by dibutyltin oxide.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 19/01/20 alle ore 20:35:46