Regioselective sulfonylation of 6,1 ',6 '-tri-O-tritylsucrose through dibutylstannylation: synthesis of 4 '-O-sulfonyl derivatives of sucrose

摘要

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 degreesC. 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 --> l)-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. (C) 2002 Elsevier Science Ltd. All rights reserved. [References: 23]