Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals.
Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good alpha selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.
Agarwal
Aditi
A
Chemistry Department, Indian Institute of Technology, Kanpur 208 016, India.
Rani
Shikha
S
Vankar
Yashwant D
YD
D002125:Calcium Gluconate / Q000737:chemistry; D002384:Catalysis; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D010472:Perchlorates / Q000737:chemistry*; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry*
D005960:Glucosides; D007202:Indicators and Reagents; D010472:Perchlorates; C002038:galactal; D058428:Silica Gel; D012822:Silicon Dioxide; D002125:Calcium Gluconate; D005690:Galactose