A simple and convenient synthetic protocol for O-isopropylidenation of sugars using bromodimethylsulfonium bromide (BDMS) as a catalyst.
Various O-isopropylidene derivatives of sugars and acyclic sugars were obtained in very good yields on reaction with acetone at room temperature with a catalytic amount of bromodimethylsulfonium bromide (BDMS). These O-isopropylidene derivatives can also be prepared in good yields on reaction with 2,2-dimethoxypropane (DMP) in acetonitrile using the same catalyst in shorter reaction times. Some of the advantages of this method are high effectiveness, a nonaqueous workup procedure, economic viability, and good yields.
Khan
Abu T
AT
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 791 039, India. atk@iitg.ernet.in
Musawwer Khan
Md
M
D000475:Alkenes / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D010100:Oxygen / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*
D000475:Alkenes; D001965:Bromides; D002241:Carbohydrates; D013450:Sulfones; C013658:propylene; D010100:Oxygen