REFERENCES
- (a) Lemieux , R. U. In Methods in Carbohydrate Chemistry ; R. L. Whistler , M. L. Wolfrom (Eds.); Academic Press Inc. : New York , 1963 ; vol. 2, pp. 221–222, and the references cited therein; (b) Lemieux , R. U. In Methods in Carbohydrate Chemistry ; R. L. Whistler , M. L. Wolfrom (Eds.); Academic Press Inc. : New York , 1963 ; vol. 2, pp. 223–224; (c) Lemieux , R. U. In Methods in Carbohydrate Chemistry ; R. L. Whistler , M. L. Wolfrom (Eds.); Academic Press Inc. : New York , 1963 ; vol. 2, pp. 224–225; (d) Fletcher Jr. , H. G. In Methods in Carbohydrate Chemistry ; R. L. Whistler , M. L. Wolfrom (Eds.); Academic Press Inc. : New York , 1963 ; vol. 2, pp. 226–228; (e) Fletcher Jr. , H. G. In Methods in Carbohydrate Chemistry ; R. L. Whistler , M. L. Wolfrom (Eds.); Academic Press Inc. : New York , 1963 ; vol. 2, pp. 228–230; For other methods, see Wang , Q. ; Fu , J. ; Zhang , J. A facile preparation of peracetylated α-aldopyranosyl chlorides with thionyl chloride and tin tetrachloride. Carbohydr. Res. 2008, 343, 2989–2991, and the references cited therein; Ibatullin , F. M. ; Selivanov , S. I. Reaction of 1,2-trans-glycosyl acetates with phosphorus pentachloride: New efficient approach to 1,2-trans-glycosyl chlorides. Tetrahedron Lett. 2002, 43, 9577–9580, and the references cited therein; see also Ref. 7.
- Wolfrom , M. L. ; Thompson , A. In Methods in Carbohydrate Chemistry ; R. L. Whistler , M. L. Wolfrom (Eds.); Academic Press Inc. : New York , 1963 ; vol. 2 , pp. 211 – 215 , and the references cited therein.
- Kartha , K. P. R. ; Field , R. A. Iodine: A versatile reagent in carbohydrate chemistry, IV: Per-O-acetylation, regioselective acylation, and acetolysis . Tetrahedron 1997 , 53 , 11753 – 11766 , and references cited therein.
- (a) Fletcher Jr. , H. G. In Methods in Carbohydrate Chemistry ; R. L. Whistler , M. L. Wolfrom (Eds.); Academic Press Inc. : New York , 1963 ; vol. 2 , pp. 234 – 237 ; (b) Van Cleve , J. W. In Methods in Carbohydrate Chemistry ; R. L. Whistler , M. L. Wolfrom , (Eds.); Academic Press Inc. : New York , 1963 ; vol. 2 , pp. 237 – 238 .
- Giri , S. K. ; Verma , M. ; Kartha , K. P. R. Indium(III) triflate: A highly efficient catalyst for reactions of sugars . J. Carbohydr. Chem. 2008 , 27 , 464 – 478 .
- (a) Gregg , B. T. ; Golden , K. C. ; Quinn , J. F. Indium(III)trifluoromethanesulfonate as a mild, efficient catalyst for the formation of acetals and ketals in the presence of acid-sensitive functional groups . Tetrahedron 2008 , 64 , 3287 – 3295 ; (b) Tran , A. T. ; Deydier , S. ; Bonnaffe , D. ; Narvor , C. L. Regioselective green anomeric deacetylation catalyzed by lanthanide triflates . Tetrhedron Lett. 2008 , 49 , 2163 – 2165 ; (c) Nakamura , M. ; Endo , K. ; Nakamura , E. Indium triflate–catalyzed vinylation of β-ketoesters with acetylene gas . Org. Lett. 2005 , 7 ( 15 ), 3279 – 3281 ; (d) Ghosh , R. ; Maiti , S. ; Chakraborty , A. ; Halder , R. Indium triflate: A reusable catalyst for expeditious chemoselective conversion of aldehydes to acylals . J. Mol. Catal. A: Chem. 2004 , 215 , 49 – 53 ; (e) Mineno , T. A fast and practical approach to tetrahydropyranylation and depyranylation of alcohols using indium triflate . Tetrahedron Lett. 2002 , 43 , 7975 – 7978 ; (f) Yadav , J. S. ; Reddy , B. V. S. ; Sadashiv , K. ; Harikishan , K. Indium triflate–catalyzed ring opening of aziridines with carboxylic acids . Tetrahedron Lett. 2002 , 43 , 2099 – 2101 ; (g) Frost , C. G. ; Hartley , J. P. ; Whittle , A. J. Indium-catalyzed aryl and alkyl sulfonylation of aromatics . Synlett 2001 , 6 , 830 – 832 ; (h) Chapman , C. J. ; Frost , C. G. ; Hartley , J. P. ; Whittle , A. J. Efficient aromatic and heteroatom acylations using catalytic indium complexes with lithium perchlorate . Tetrahedron Lett. 2001 , 42 , 773 – 775 ; (i) Chauhan , K. K. ; Frost , C. G. Advances in indium-catalyzed organic synthesis . J. Chem. Soc., Perkin Trans. 1 , 2000 , 3015 – 3019 ; (j) Prajapati , D. ; Laskar , D. D. ; Sandhu , J. S. Indium trifluoromethanesulfonate [In(OTf)3]: A novel reusable catalyst for intramolecular Diels–Alder reactions . Tetrahedron Lett. 2000 , 41 , 8639 – 8643 ; (k) Li , C.-J. ; Chan , T.-H. Organic syntheses using indium-mediated and catalyzed reactions in aqueous media . Tetrahedron 1999 , 55 , 11149 – 11176 ; (l) Chauhan , K. K. ; Frost , C. G. ; Love , I. ; Waite , D. Indium triflate: An efficient catalyst for acylation reactions . Synlett 1999 , 11 , 1743 – 1744 ; (m) Kobayashi , S. ; Nagayama , S. ; Busujima , T. Lewis acid catalysts stable in water: Correlation between catalytic activity in water and hydrolysis constants and exchange rate constants for substitution of Inner-sphere water ligands . J. Am. Chem. Soc. 1998 , 120 , 8287 – 8288 ; (n) Cintas , P. Synthetic organoindium chemistry: What makes indium so appealing? Synlett 1995 , 1087 – 1096 .
- Montero , J.-L. ; Winum , J.-Y. ; Leydet , A. ; Kamal , M. ; Pavia , A. A. ; Roque , J.-P. A convenient synthesis of peracetylated glycosyl halides using bismuth(III) halides as catalysts. Carbohydr. Res. 1997, 297, 175–180.
- Brauns , D. H. Fluoro-acetyl derivatives of sugars. III. Optical rotation and atomic dimension (continued) . J. Am. Chem. Soc. 1924 , 46 , 1484 – 1488 .
- Kovács , G. ; Micskei , K. ; Somsák , L. Preparation of acetylated pyranoid glycals from glycosyl halides by chromium(II) complexes under aqueous biphasic conditions . Carbohydr. Res. 2001 , 336 , 225 – 228 .
- Xue , W. ; Cheng , X. ; Fan , J. ; Diao , H. ; Wang , C. ; Dong , L. ; Luo , Y. ; Chen , J. ; Zhang , J. A novel stereoselective synthesis of 1,2-trans-thioaldoses . Tetrahedron Lett. 2007 , 48 , 6092 – 6095 .
- Dick , W. E. ; Wesleder , D. Facile synthesis of 1,2-trans-O-acetylglycosyl chloride derivatives of cellobiose, lactose, and D-glucose . Carbohydr. Res. 1976 , 46 ( 2 ), 173 – 182 .
- Ness , R. K. ; Fletcher Jr. , H. G. ; Hudson , C. S. The reaction of 2,3,4,6-tetrabenzoyl-α-D-glucopyranosyl bromide and 2,3,4,6-tetrabenzoyl-α-D-mannopyranosyl bromide with methanol: Certain benzoylated derivatives of D-glucose and D-Mannose . J. Am. Chem. Soc. 1950 , 72 , 2200 – 2205 .
- Durette , P. L. ; Horton , D. Conformational studies on pyranoid sugar derivatives by NMR spectroscopy: Conformational equilibriums of some peracetylated aldopentopyranosyl halides in solution . Carbohydr. Res. 1971 , 18 , 57 – 80 .
- Fletcher Jr. , H. G. ; Hudson , C. S. The reactions of tribenzoyl-β-D-arabinopyranosyl bromide and tribenzoyl-α-D-xylopyranosyl bromide with methanol . J. Am. Chem. Soc. 1950 , 72 , 4173 – 4177 .
- Yoon , S. ; Kim , D. ; Shin , J. E. N. A facile synthesis of p-nitrophenyl glycosides . Bull. Korean Chem. Soc. 1994 , 15 , 559 – 563 .
- Polat , T. ; Linhardt , R. J. Zinc triflate–benzoyl bromide: A versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides . Carbohydr. Res. 2003 , 338 , 447 – 449 .
- Presented in part at CARBO-XXII, Meeting of the Association of Carbohydrate Chemists and Technologists India, 13–15 December 2007, NIPER, S.A.S. Nagar, India.