An efficient synthesis of 2,3-dideoxy-alpha,beta-unsaturated carbohydrate enals by mixed Lewis acid (HfCl4 and ZnI2) catalyzed hydration of glycals.
A new, efficient method has been developed for converting acyl-, arylalkyl- and alkyl-protected glycals into corresponding 2,3-dideoxy-alpha,beta-unsaturated carbohydrate enals utilizing the in situ generated push-pull effect resulting from the synergistic combination of HfCl4 and ZnI2 in catalytic amounts. This new procedure eliminates the use of highly toxic Hg2+ ions and acidic conditions (0.01-0.02 N H2SO4), besides radically shortening the reaction time.
Saquib
Mohammad
M
Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226 001, India.
Sagar
Ram
R
Shaw
Arun K
AK
D000143:Acids / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006195:Hafnium / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014867:Water / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry*
D000143:Acids; D000447:Aldehydes; D002241:Carbohydrates; D007454:Iodides; D017967:Zinc Compounds; D014867:Water; C029770:zinc iodide; D006195:Hafnium