http://www.cnr.it/ontology/cnr/individuo/prodotto/ID236927

Total Synthesis of 1,5-Dideoxy-1,5-iminoalditols (Articolo in rivista)

Type

Label

Total Synthesis of 1,5-Dideoxy-1,5-iminoalditols (Articolo in rivista) (literal)

Anno

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Alternative label

Gloria Rassu,* Luigi Pinna, Pietro Spanu, Nicola Culeddu, Giovanni Casiraghi, Giovanna Gasparri Fava, Marisa Belicchi Ferrari, and Giorgio Pelosi (1992)
Total Synthesis of 1,5-Dideoxy-1,5-iminoalditols
in Tetrahedron (Oxf., Print); Elsevier, Oxford (Regno Unito)
(literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

Gloria Rassu,* Luigi Pinna, Pietro Spanu, Nicola Culeddu, Giovanni Casiraghi, Giovanna Gasparri Fava, Marisa Belicchi Ferrari, and Giorgio Pelosi (literal)

Pagina inizio

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Rivista

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Dipartimento di Chimica dell'Universita' and Istituto per I'Applicazione delle Tecniche Chimiche Avanzate del CNR Via Vienna, 2 I-07100 Sassari, Italy Istituto di Chimica Generale dell'Universita' and Centro di Studio per la Struttura Diffrattometrica del CNR, Viale delle Scienze 1, I-43100 Parma, Italy (literal)

Titolo

Abstract

Enantiomerically pure 1,5-dideoxy-I ,5-imino-D -glycero-D -allo-heptitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-Dglyceraldehyde- N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4. followed by diastereoselective anticisdihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9. (literal)

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