Iodine-sodium cyanoborohydride-mediated reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides.
A quick, efficient and convenient method for the regiospecific reductive ring opening of 4,6-O-benzylidene acetals of O-/S-alkyl/aryl glycosides of mono- and disaccharides, leading to the exclusive formation of the corresponding 6-O-benzyl ethers, using sodium cyanoborohydride in the presence of molecular iodine, is reported. It has been observed that common protecting groups such as ethers and esters are well tolerated under the conditions studied. The reaction was proved unsuccessful when applied to a glucosamine-derived benzylidene acetal.
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, S.A.S. Nagar, Punjab, India.
Kaki Venkata
KV
Rao
Premanand R
PR
Patil
Sridhar
S
Atmakuri
K P Ravindranathan
KP
Kartha
D001597:Benzylidene Compounds / Q000737:chemistry*; D001894:Borohydrides / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure
D001597:Benzylidene Compounds; D001894:Borohydrides; D007455:Iodine; C009282:sodium cyanoborohydride