Indium(III) triflate: A highly efficient catalyst for reactions of sugars

Journal of Carbohydrate Chemistry

Volumn 27, Issue 8-9, 2008, Pages 464-478

  Giri, Santosh Kumar ^a   Verma, Monika ^a   Kartha, K P Ravindranathan ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Acetal formation and hydrolysis; Acyl transfer reactions; Indium(III) triflate; Thioglycosylation

Indexed keywords

EID: 57649167433     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300802458970     Document Type: Article

References (51)

1. Giri, S.K.; Verma, M.; Kartha, K.P.R. Presented at the CARBO XXI, Meeting of the Association of Carbohydrate Chemists and Technologists India, 26-29 Nov. 2006, New Delhi, India.
2. Frost, C.G.; Chauhan, K.K. Advances in indium-catalysed organic synthesis. J. Chem. Soc. Perkin Trans 1, 2000, 3015-3019.
3. 3). A novel reusable catalyst for intramolecular Diels-Alder reactions, Tetrahedron Lett. 2000, 41, 8639-8643;
4. (b) Ghosh, R.; Maiti, S.; Chakraborty, A.; Haider, R. Indium triflate: a reusable catalyst for expeditious chemoselective conversion of aldehydes to acylals. J. Mol. Catal. A Chem. 2004, 215, 49-53.
5. (a) Cintas, P. Synthetic organoindium chemistry: what makes indium so appealing? Synlett, 1995, 1087-1096;
6. (b) Li, C.J.; Chan, T.H. Organic syntheses using indium-mediated and catalyzed reactions in aqueous media. Tetrahedron 1999, 55, 11149-11176;
7. (c) Ranu, B.C. Indium metal and its halides in organic synthesis. Eur. J. Org. Chem. 2000, 2347-2356;
8. (d) Li, C.J. Aqueous Barbier-Grignard type reaction: scope, mechanism, and synthetic applications. Tetrahedron 1996, 52, 5643-5668.
9. Mineno, T. A fast and practical approach to tetrahydropyranylation and depyranylation of alcohols using indium triflate. Tetrahedron Lett. 2002, 43, 7975-7978.
10. Chauhan, K.K.; Frost, C.G.; Love, I.; Waite, D. Indium triflate: An efficient catalyst for acylation reaction. Synlett 1999, 1743-1744.
11. 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.
12. Frost, C.G.; Hartley, J.P.; Whittle, A.J. Indium-catalysed aryl and alkyl sulfonylation of aromatics. Synlett 2001, 6, 830-832.
13. 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.
14. 3-catalyzed mild cleavage of isopropylidene acetals in Tricky substrates. Tetrhedron Lett. 2008, 49, 1961-1964) have been published.
15. Dasgupta, F.; Singh, P.P.; Srivastava, H.C. Acetylation of carbohydrates using ferric chloride in acetic anhydride. Carbohydr. Res. 1980, 80, 346-349. Also see: Vogel, A.I. In Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Pearson Education: Singapore, 1989, pp. 644-651; Wolfrom, M.L.; Thomson, A. Acetylation. Methods Carbohydr. Chem. 1963, 2, 211-215.
16. 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. See also: Kartha, K.P.R.; Dasgupta, F; Singh, P.P.; Srivastava, H.C. Use of ferric chloride in carbohydrate reactions IV. Acetolysis of benzyl ethers of sugars. J. Carbohydr. Chem. 1986, 5, 437-444.
17. (a) Jansson, K.; Ahlfors, S.; Frejd, T.; Kihlberg, J.; Magnusson, G. 2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars J. Org. Chem. 1988, 53, 5629-5647;
18. b) Jansson, K.; Frejd, T.; Kihlberg, J.; Magnusson, G. 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. 1986, 27, 753-756.
19. Kartha, K.P.R.; Kiso, M.; Hasegawa, A. Synthetic studies on sialoglycoconjugates 9: An efficient method for the selective acetolysis of 2-(trimethylsilyl)ethyl glycosides using ferric chloride in acetic anhydride. J. Carbohydr. Chem. 1989, 8, 675-679.
20. Szarek, W.A.; Zamojski, A.; Tiwari, K.N.; Ison, E.R. A new, facile method for cleavage of acetals and dithioacetals in carbohydrate derivatives. Tetrahedron Lett. 1986, 27, 3827-3830.
21. Lemieux, R.U; Takeda, T.; Chung, B.Y. Synthetic Methods for Carbohydrates, ACS Symposium Series No. 39, H.S.L. Khadem Ed., Am. Chem. Soc: Washington, D.C., 1976, 90-115.
22. Pozsgay, V.; Jennings, H.J. Synthesis of a di-, tri-, and tetra-saccharide unit of the group B streptococcal common antigen. Carbohydr. Ees. 1988, 179, 61-75.
23. Hudson, C.S.; Dale, J.K. The isomeric tetracetates of 1-arabinose and beta-triacetyl-methyl-l-arabinoside. J. Am. Chem. Soc. 1918, 40, 992-997.
24. Wu, H.; Shen, Y.; Fan, Li-Yan; Wan, Y.; Shi, Da-Qing. Solid silica sulfuric acid (SSA) as a novel and efficient catalyst for acetylation of aldehydes and sugars. Tetrahedron 2006, 62, 7995-7998.
25. Hudson, C.S.; Dale, J.K. Triacetyl-d-xylose and alpha triacetylmethyl-d-xyloside. J. Am. Chem. Soc. 1918, 40, 997-1001.
26. Kartha, K.P.R.; Cura, P.; Aloui, M.; Readman, S.K.; Rutherford, T.J.; Field, R.A. Observations on the activation of methyl thioglycosides by iodine and its interhalogen compounds. Tetrahedron: Asymm. 2000, 11, 581-593.
27. Posner, G.H.; Haines, S.R. A convenient, one-step, high-yield replacement of an anomeric hydroxyl group by a fluorine atom using dast. Preparation of glycosyl fluorides. Tetrahedron Lett. 1985, 26, 5-8.
28. Hayashi, M.; Hashimoto, S.; Noyori, S. Simple synthesis of glycosyl fluorides. Chem. Lett. 1984, 1747-1750.
29. Gomez, A.M.; Danelon, G.O.; Valverde, D.S.; Lopez, C. Improved synthesis of 2,3:4,6-di-O-isopropylidene-D-glucopyranose and -D-galactopyranose. Carbohydr. Res. 1999, 320, 138-142.
30. Schmidt, O.T Isopropylidene derivatives. Methods Carbohydr. Chem. 1963, 2, 318-325.
31. Hanaya, T.; Sato, N.; Yamamoto, H. An efficient synthesis of methyl 1,3-O-isopro-pylidene-α-D-fructofuranoside and 2,3:5,6-di-O- isopropylidene-D-glucose dimethyl acetal derivatives from sucrose. Carbohydr. Res. 2005, 340, 2494-2501.
32. Bonner, W.A.; Hurd, CD.; Cantor, S.M. Crystalline 2,3,4,6-Tetrapropionyl- β-D-glucose. J. Am. Chem. Soc. 1947, 69, 1816-1819.
33. Hurd, CD.; Liggett, R.W Analytical separation of sugars by distillation of their propionates. J. Am. Chem. Soc. 1941, 63, 2659-2662.
34. Lam, S.N.; Gervay-Hague, J. Solution- and solid-phase oligosaccharide synthesis using glucosyl iodides: a comparative study. Carbohydr. Res. 2002, 337, 1953-1965.
35. Hugo Norberto, C.; Manuel, M.L.; Manuel, B. Syntheses and insulin-like activity of phosphorylated galactose derivatives. Carbohydr. Res. 1993, 240, 119-131.
36. Shiro, K; Hideharu, I.; Makoto, K; Akira, H. Synthesis of deoxygalactose-containing sialyl Le(X) ganglioside analogues to elucidate the structure necessary for selectin recognition. Glycoconjugate J. 1996, 13, 241-254.
37. 3. MALDI-TOF found 567.235, required 567.24 [M+Na]+.
38. Magnusson, G. 2-(Trimethylsilyl)ethyl (TMSEt) glycosides; anomeric blocking, deblocking and activation in the synthesis of oligosaccharides. Trends Glycosci. Glycotechnol. 1992, 4, 358-367.
39. Singh, P.P.; Gharia, M.M.; Dasgupta, F.; Srivastava, H.C. Use of ferric chloride in carbohydrate chemistry. I. A quick method for the preparation of O-isopropylidene derivatives of Carbohydrates. Tetrahedron Lett. 1977, 5, 439-440.
40. Levene, P.A.; Tipson, R.S. An improved method for the preparation of xylulose and ribulose. J. Biol. Chem. 1936, 115, 731-747.
41. Baer, E.; Fischer, H.O.L. Studies on acetone-glyceraldehyde. IV. Preparation of d(+)-acetone glycerol. J. Biol. Chem. 1939, 128, 463-473.
42. Attolino, E.; Fairbanks, A.J. β-Mannosylation of N-acetyl glucosamine by propargyl mediated intramolecular aglycon delivery (IAD): synthesis of the N-glycan core pentasaccharide. Tetrahedron Lett. 2007, 48, 3061-3064.
43. Rye, C.S.; Withers, S.G. Elucidation of the mechanism of polysaccharide cleavage by chondroitin AC lyase from Flavobacterium heparinum. J. Am. Chem. Soc. 2002, 124, 9756-9767.
44. Katsumi, A.; Ichiro, M.; Mayumi, S. Preparation of sugars and (thio)glycoside derivatives as intermediates for oligosaccharides, glycolipides, and glycoprotines. Chem. Abstracts 1994, 121, 1146.
45. Barili, P.L.; Berti, G.; Catelani, G.; Colonna, F.; Marra, A. New results in the isopropylidenation of galactopyranosides. Useful intermediates for the synthesis of galactose derivatives. Tetrahedron Lett. 1986, 27, 2307-2310.
46. 4 supported on silica gel. Carbohydr. Res. 2005, 340, 1661-1667.
47. Johansson, R.; Samuelsson, B. Regioselective reductive ring-opening of 4-methoxybenzylidene acetals of hexopyranosides. Access to a novel protecting-group strategy. Part 1. J. Chem. Soc. Perkin Trans 1 1984, 2371-2374.
48. Robertson, J.; Stafford, P.M. Selective hydroxyl protection and deprotection. In Best Synthetic Methods; Carbohydrates 1st ed.; Harwood, L. M., eds.; Academic Press; New York, 2003, 9-65.
49. Hasegawa, A.; Ogawa, M.; Ishida, H.; Kiso, M. Synthetic studies on sialoglycoconjugates 16: α-predominant glycoside synthesis of N-acetylneuraminic acid with the primary hydroxyl group in carbohydrates using dimethyl(methylthio)sulfonium triflate as a glycosyl promoter. J. Carbohydr. Chem. 1990, 9, 393-414.
50. 4reagent under two-phase conditions. Tetrahedron Lett. 1999, 40, 8439-8441.
51. Kojima, M.; Nakamura, Y. A practical fluorous benzylidene acetal protecting group for a quick synthesis of disaccharides. Tetrahedron Lett. 2007, 48, 4431-4436.