Synthesis of 4-deoxy-L-(and D-)hexoses from chiral noncarbohydrate building blocks.
4-Deoxy-l-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their d-series enantiomers.
Caputo
Romualdo
R
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Via Cynthia, 4 80126 Naples, Italy.
De Nisco
Mauro
M
Festa
Pasquale
P
Guaragna
Annalisa
A
Palumbo
Giovanni
G
Pedatella
Silvana
S
D003837:Deoxy Sugars / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D006601:Hexoses / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003837:Deoxy Sugars; D004852:Epoxy Compounds; D006601:Hexoses; C020344:glycidyl ethers