Regioselective sulfonylation of 6,1',6'-tri-O-tritylsucrose through dibutylstannylation: synthesis of 4'-O-sulfonyl derivatives of sucrose.
3-O-Mesyl-1,6-di-O-trityl-beta-D-fructofuranosyl-(2-->1)-6-O-trityl-alpha-D-glucopyranoside (3) was synthesized via stannylation of 6,1',6'-tri-O-tritylsucrose with dibutyltin oxide in benzene, followed by treatment of the crude product with methanesulfonyl chloride in the presence of triethylamine in dichloromethane at 0 degrees C. A similar treatment of the tri-tritylsucrose in toluene, instead of benzene, yielded 4-O-mesyl-1,6-di-O-trityl-beta-D-fructofuranosyl-(2-->1)-6-O-trityl-alpha-D-glucopyranoside (4) as the major product. The X-ray crystal structure of the corresponding acetyl derivative, 3-O-acetyl-4-O-mesyl-1,6-di-O-trityl-beta-D-fructofuranosyl-(2-->1)-2,3,4-tri-O-acetyl-6-O-trityl-alpha-D-glucopyranoside (5), confirms the position and stereochemistry of the methanesulfonyl group at C-4 of the fructofuranosyl ring.
Sofian
A S Muhammad
AS
Department of Chemistry, National University of Singapore, Kent Ridge, Singapore 119260. scip8192@nus.edu.sg
Lee
Cheang Kuan
CK
Linden
Anthony
A
D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009947:Organotin Compounds; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013450:Sulfones / Q000138:chemical synthesis*; D014320:Triphenylmethyl Compounds
D009947:Organotin Compounds; D013450:Sulfones; D014320:Triphenylmethyl Compounds; C056189:di-n-butyltin; D013395:Sucrose