Unprecedented Transformation of Thioglycosides to Their Corresponding 1‐O‐Acetates in the Presence of HClO₄‐SiO₂Footnote§

^§C.D.R.I. communication no. 6979.

References

• Dwek , R. A. 1996 . Glycobiology: towards understanding the function of sugar . Chem. Rev. , 96 : 683 – 720 .
   PubMed Web of Science ®Google Scholar
• Hanessian , S. 1996 . Preparative Carbohydrate Chemistry Edited by: Hanessian , S. 1 – 636 . New York : Marcel Dekker .
   Google Scholar
• Norberg , T. 1995 . “ Modern Methods in Carbohydrate Synthesis ” . In Frontiers in Natural Product Research Series Edited by: Khan , S. H. and O'Neill , R. A. Vol. 1 , 82 – 106 . Harwood Academic . Chapter 4
   Google Scholar
• Garegg , P. J. 1997 . Thioglycosides as glycosyl donors in oligosaccharide synthesis . Adv. Carbohydr. Chem. Biochem. , 52 : 179 – 205 .
   PubMed Web of Science ®Google Scholar
• Kiso , M. and Anderson , L. 1979 . The synthesis of disaccharides by the ferric chloride‐catalyzed coupling of 2‐acylamido‐2‐deoxy‐β‐D‐glucopyranose 1‐acetates to protect sugar acceptors . Carbohydr. Res. , 72 : C15 – C17 .
   Google Scholar
• Dahmen , J. , Frejd , T. , Magnusson , G. and Noori , G. 1983 . Boron trifluoride etherate‐induced glycosidation: formation of alkyl glycosides and thioglycosides of 2‐deoxy‐2‐phthalimidoglycopyranoses . Carbohydr. Res. , 114 : 328 – 330 .
   Web of Science ®Google Scholar
• Paulsen , H. and Paal , M. 1984 . Lewissäure‐katalysierte synthesen von di‐ und trisaccharid‐sequenzen der O‐ und N‐glycoproteine. Anwendung von trimethylsilyltrifluoromethanesulfonat . Carbohydr. Res. , 135 : 53 – 69 .
   Web of Science ®Google Scholar
• Scheurer , P. G. and Smith , F. 1954 . Synthesis of acetobromo sugars . J. Am. Chem. Soc. , 76 : 3224 – 3224 .
   Web of Science ®Google Scholar
• Jain , R. K. , Piskorz , C. F. , Chandrasekharan , E. V. and Matta , K. L. 1995 . Synthesis of benzyl‐O‐(3‐O‐methyl‐β‐D‐galactopyranosyl)‐(1→3)‐2‐acetamido‐2‐deoxy‐α‐D‐galactopyrano‐side and benzyl O‐(β‐D‐galactopyranosyl)‐(1→3)‐2‐acetamido‐2‐deoxy‐6‐O‐methyl‐α‐D‐galactopyranoside as specific acceptors for sialyltransferases . Carbohydr. Res. , 271 : 247 – 251 .
   Google Scholar
• Nishimura , S. I. and Kuzuhara , H. 1990 . Synthesis of a peripheral trisaccharide sequence of lutropin, a pituitary glycoprotein hormone; use of chitobiose as a key starting material . Carbohydr. Res. , 206 : 207 – 217 .
   PubMed Web of Science ®Google Scholar
• Misra , A. K. , Basu , S. and Roy , N. 1996 . Synthesis of the immunodominant trisaccharide related to the antigen from E. coli O126 . Synth. Commun. , 26 : 2857 – 2862 .
   Web of Science ®Google Scholar
• Zhang , Z. and Magnusson , G. 1996 . Conversion of p‐methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides . Carbohydr. Res. , 295 : 41 – 55 .
   PubMed Web of Science ®Google Scholar
• Jansson , K. , Frejd , T. , Kihlberg , J. and Magnusson , G. 1986 . Boron trifluoride etherate as an effective reagent for the stereoselective one‐pot conversion of acetylated 2‐trimethylsilylethyl glycosides into sugar 1,2‐trans‐acetates . Tetrahedron Lett. , 27 : 753 – 756 .
   Web of Science ®Google Scholar
• Misra , A. K. and Agnihotri , G. 2004 . Chloramine‐T‐mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions . Carbohydr. Res. , 339 : 885 – 890 . and references cited therein
   PubMed Web of Science ®Google Scholar
• Leigh , D. A. , Smart , J. P. and Truscello , A. M. 1995 . Intermolecular aglycon transfer of ethyl 1‐thiorhamnopyranosides under Koenigs‐Knorr and Helferich glycosylation conditions . Carbohydr. Res. , 276 : 417 – 424 .
   PubMed Web of Science ®Google Scholar
• Belot , F. and Jacquinet , J. 1996 . Intermolecular aglycon transfer of a phenyl 1‐thiogalactosaminide derivative under trichloroacetimidate glycosylation conditions . Carbohydr. Res. , 290 : 79 – 86 .
   PubMed Web of Science ®Google Scholar
• Yu , H. , Yu , B. , Wu , X. , Hui , Y. and Han , X. 2000 . Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors . J. Chem. Soc., Perkin Trans. 1 , : 1445 – 1453 .
   Google Scholar
• Zhu , T. and Boons , G.‐J. 2000 . Intermolecular aglycon transfer of ethyl thioglycosides can be prevented by judicious choice of protecting groups . Carbohydr. Res. , 329 : 709 – 715 .
   Google Scholar
• Misra , A. K. , Tiwari , P. and Madhusudan , S. K. 2005 . HClO4‐SiO2 catalyzed per‐O‐acetylation of carbohydrates . Carbohydr. Res. , 340 : 325 – 329 .
   PubMed Web of Science ®Google Scholar
• Misra , A. K. , Tiwari , P. and Agnihotri , G. 2005 . Ferrier rearrangement catalyzed by HClO4‐SiO2: synthesis of 2,3‐unsaturated glycopyranosides . Synthesis , 2 : 260 – 266 .
   Web of Science ®Google Scholar
• Tiwari , P. , Agnihotri , G. and Misra , A. K. 2005 . Synthesis of 2,3‐unsaturated C‐glycosides by HClO4‐SiO2 catalyzed Ferrier rearrangement of glycols . Carbohydr. Res. , 340 : 749 – 752 .
   Google Scholar
• Kumar , R. , Tiwari , P. , Maulik , P. R. and Misra , A. K. 2005 . HClO4‐SiO2 catalyzed chemoselective synthesis of acylals from aldehydes under solvent‐free conditions . J. Mol. Cat. A: Chemical , 247 : 27 – 30 .
   Google Scholar
• Tiwari , P. and Misra , A. K. 2006 . Selective removal of anomeric O‐acetate groups in carbohydrates using HClO4‐SiO2 . Tetrahedron Lett. , 47 : 3573 – 3576 .
   Web of Science ®Google Scholar
• Tai , A.‐A. , Kulkarni , S. S. and Hung , S.‐C. 2003 . Facile Cu(OTf)2‐catalyzed preparation of per‐O‐acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one‐pot anomeric substitution to thioglycosides under solvent‐free conditions . J. Org. Chem. , 68 : 8719 – 8722 .
   PubMed Web of Science ®Google Scholar
• Lemieux , R. U. , Takeda , T. and Chung , B. Y. 1976 . Synthetic Methods for Carbohydrates Edited by: El Khadem , H. S. Vol. 39 , 90 – 115 . American Chemical Society . ACS Symposium Series
   Google Scholar
• Austin , P. W. , Hardy , F. E. , Buchanan , J. G. and Baddiley , J. 1965 . 2,3,4,6‐Tetra‐O‐benzyl‐D‐galactosyl chloride and its use in the synthesis of α and β‐D‐galactopyranosides . J. Chem. Soc. , : 1419 – 1424 .
   Google Scholar
• Bhaskar , P. M. and Loganathan , D. 1998 . Per‐O‐acetylation of sugars catalysed by montmorillonite K‐10 . Tetrahedron Lett. , 39 : 2215 – 2218 .
   Web of Science ®Google Scholar
• Chen , C.‐T. , Kuo , J.‐H. , Li , C.‐H. , Barhate , N. B. , Hon , S.‐W. , Li , T.‐W. , Chao , S.‐D. , Liu , C.‐C. , Li , Y.‐C. , Chang , I.‐H. , Lin , J.‐S. , Liu , C.‐J. and Chou , Y.‐C. 2001 . Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate . Org. Lett. , 3 : 3729 – 3732 .
   PubMedGoogle Scholar
• Das , S. K. , Reddy , K. A. , Krovvidi , V. L.N.R. and Mukkanti , K. 2005 . InCl3 as a powerful catalyst for the acetylation of carbohydrate alcohols under microwave irradiation . Carbohydr. Res. , 340 : 1387 – 1392 .
   PubMed Web of Science ®Google Scholar