A versatile route to L-hexoses: synthesis of L-mannose and L-altrose.
[reaction: see text] An efficient route for the synthesis of orthogonally protected l-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-l-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-l-pyranoside, which can be suitably functionalized to afford the desired l-hexoses. In this paper, we report the synthesis of l-manno- and l-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.
Guaragna
Annalisa
A
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cynthia, 4 I-80126 Napoli, Italy. guaragna@unina.it
Napolitano
Carmela
C
D'Alonzo
Daniele
D
Pedatella
Silvana
S
Palumbo
Giovanni
G
D002384:Catalysis; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D006601:Hexoses; D008358:Mannose