Synthesis of (+)-(2R,3S,4R)-2,3,4-trihydroxycyclohexanone from D-glucose.
We have described the synthesis of (+)-(2R,3S,4R)-2,3,4-trihydroxycyclohexanone by the reduction of a keto-conduritol derivative, the latter being prepared in five steps from (-)-(2S,3R,4S,5S)-2,3,4-tribenzyloxy-5-hydroxycyclohexanone, which is in turn readily synthesized from D-glucose.
Carvalho
Ivone
I
Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café s/n, Monte Alegre, 14040-903 Ribeirão, Preto, SP, Brazil. carronal@usp.br
de Melo
Eduardo B
EB
D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry*; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
C489873:2,3,4-trihydroxycyclohexanone; D003511:Cyclohexanols; D003512:Cyclohexanones; D005947:Glucose