Iodine monochloride/silver trifluoromethanesulfonate (ICI/AgOTf) as a convenient promoter system for O-glycoside synthesis

Organic Letters

Volumn 3, Issue 6, 2001, Pages 913-915

  Ercegovic, Teddy ^a   Meijer, Andreas ^a   Magnusson, Göran ^a   Ellervik, Ulf ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCOSIDE; IODIDE; IODINE MONOCHLORIDE; MESYLIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION; KINETICS; SYNTHESIS;

CHLORIDES; GLYCOSIDES; GLYCOSYLATION; INDICATORS AND REAGENTS; IODIDES; KINETICS; MESYLATES; MOLECULAR STRUCTURE;

EID: 0035932570     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015547c     Document Type: Article

References (23)

1. (a) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 2000, 14, 2137-2160.
2. (b) DeNinno, M. P. Synthesis 1991, 583-593.
3. Carbohydrate Chemistry, 1st ed.; Boons, G.-J., Ed.; Blackie Academic & Professional: London, 1998; and references therein.
4. (a) Modern Methods in Carbohydrate Synthesis; Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: Amsterdam, 1996.
5. (b) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker New York, 1997.
6. Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 1702-1706.
7. Dasgupta, F.; Garegg, P. J. Carbohydr. Res. 1988, 177, C13-C17.
8. (a) Veeneman, G. H.; Van Leeuwen, S. H.; Van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334.
9. (b) Konradsson, P.; Mootoo, D. R.; McDevitt, R. E.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1990, 270-272.
10. Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313-4316.
11. (a) Turek, D. Ph.D. Thesis, Stockholm University, Stockholm, Sweden, 2000.
12. (b) Andersson, M.; Konradsson, P.; Oscarsson, S.; Öhberg, L. J. Carbohydr. Chem., in press.
13. (a) Ravindranathan Kartha, K. P.; Cura, P.; Aloui, M.; Readman, S. K.; Rutherford, T. J.; Field, R. A. Tetrahedron: Asymmetry. 2000, 11, 581-593.
14. (b) Ravindranathan Kartha, K. P.; Field, R. A. Tetrahedron Lett. 1997, 38, 8233-8236.
15. Iodine monochloride is commercially available as a dry 1.0 M solution in dichloromethane. Silver trifluoromethanesulfonate is soluble in acetonitrile and easily dried in vacuo. The entire procedure is substantially free from offensive odors.
16. Representative Experimental Procedure. A stirred solution of ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β- D-glucopyranoside (1; 76 mg, 0.15 mmol) and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (2; 50 mg, 0.10 mmol) in dichloromethane (0.75 mL) was cooled to -45°C under an argon atmosphere. A solution of silver trifluoromethanesulfonate (77 mg, 0.30 mmol) in acetonitrile (0.50 mL) was added followed by dropwise addition of a 1.0 M solution of iodine monochloride in dichloromethane (0.25 mL, 0.25 mmol) during 10 min. After 2 h, diisopropylamine (0.20 mL, 1.4 mmol) was added and stirring was continued for 20 min. The reaction mixture was filtered and concentrated under reduced pressure. The residue was chromatographed (heptane/ethyl acetate, 3:1 → 1:1) on silica gel to give 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2- trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-β-D-glucopyranoside (3; 78.2 mg, 82%) as a syrup.
17. Jacob, L. A.; Chen, B. L.; Stec, D. Synthesis 1993, 6, 611-614.
18. Using MeSBr/AgOTf as alternative promoter system gave the same diastereomeric ratio, and the mixture was inseparable by conventional silica gel chromatography.
19. Ellervik, U.; Magnusson, G. Carbohydr. Res. 1996, 280, 251-260.
20. Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314-9322.
21. Marra, A.; Sinay, P. Carbohydr. Res. 1990, 195, 303-308.
22. Wilstermann, M.; Kononov, L. O.; Nilsson, U.; Ray, A. K., Magnusson, G. J. Am. Chem. Soc. 1995, 117, 4742-4754. The crude product was acetylated to facilitate purification.
23. Ercegovic, T. Ph.D. Thesis, The Lund Institute of Technology, University of Lund, Lund, Sweden, 2001, in press. Available at http:// www.lub.lu.se/dissdb/ in pdf format as of February 27, 2001.