Please use this identifier to cite or link to this item: https://doi.org/10.1016/S0008-6215(02)00347-6
Title: Regioselective sulfonylation of 6,1′,6′-tri-O-tritylsucrose through dibutylstannylation: Synthesis of 4′-O-sulfonyl derivatives of sucrose
Authors: Sofian, A.S.M.
Lee, C.K. 
Linden, A.
Keywords: Methanesulfonate
Stannylation
Sucrose
Trifluoromethanesulfonate
Issue Date: 29-Nov-2002
Source: Sofian, A.S.M., Lee, C.K., Linden, A. (2002-11-29). Regioselective sulfonylation of 6,1′,6′-tri-O-tritylsucrose through dibutylstannylation: Synthesis of 4′-O-sulfonyl derivatives of sucrose. Carbohydrate Research 337 (24) : 2377-2381. ScholarBank@NUS Repository. https://doi.org/10.1016/S0008-6215(02)00347-6
Abstract: 3-O-Mesyl-1,6-di-O-trityl-β-D-fructofuranosyl-(2→1)-6-O-trityl- α-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°C. A similar treatment of the tri-tritylsucrose in toluene, instead of benzene, yielded 4-O-mesyl-1,6-di-O-trityl-β-D-fructofuranosyl-(2→1)-6-O-trityl- α-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-β-D-fructofuranosyl-(2→1)-2, 3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside (5), confirms the position and stereochemistry of the methanesulfonyl group at C-4 of the fructofuranosyl ring. © 2002 Elsevier Science Ltd. All rights reserved.
Source Title: Carbohydrate Research
URI: http://scholarbank.nus.edu.sg/handle/10635/76879
ISSN: 00086215
DOI: 10.1016/S0008-6215(02)00347-6
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