Improved catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate: application to various 1-hydroxy sugars

Carbohydrate Research

Volumn 345, Issue 6, 2010, Pages 740-749

  Shirahata, Tatsuya ^a   Matsuo, Jun ichi ^b   Teruya, Satoko ^a   Hirata, Nozomu ^a   Kurimoto, Taku ^a   Akimoto, Nanao ^a   Sunazuka, Toshiaki ^a   Kaji, Eisuke ^a   Omura, Satoshi ^a  

^a KITASATO UNIVERSITY   (Japan)

^b KITASATO INSTITUTE   (Japan)

Author keywords

Glycosylation; Lewis acids; Solvent effects; Synthetic methods

Indexed keywords

CATALYTIC AMOUNTS; GLYCOSYL; GLYCOSYL ACCEPTORS; LEWIS ACID; ONE POT; SOLVENT EFFECTS; STEREO-SELECTIVE; SYNTHETIC METHODS; TRICHLOROACETYL ISOCYANATES;

ACIDS; CARBOHYDRATES; CHEMICAL ACTIVATION; GLYCOSYLATION; MOLECULAR SIEVES; SIEVES; STEREOSELECTIVITY; SUGAR (SUCROSE);

ESTERIFICATION;

2,3 DI O BENZYL 4,6 O BENZYLIDENE DEXTRO MANNOPYRANOSYL N TRICHLOROACETYLCARBAMATE; 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO MANNOPYRANOSYL N TRICHLOROACETYLCARBAMATE; 2,3,4,6 TETRA O BENZYL BETA DEXTRO MANNOPYRANOSYL N TRICHLOROACETYLCARBAMATE; 2,3,4,6 TETRA O BENZYL DEXTRO GLUCOPYRANOSYL N TRICHLOROACETYLCARBAMATE; 3 O (2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO GLUCOPYRANOSYL)CHOLESTEROL; CARBAMIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; GLYCOSYL N TRICHLOROACETYLCARBAMATE; ISOPROPYL 4 O ACETYL 3 O (TERT BUTYLDIMETHYLSILYL) 6 BROMO 6 DEOXY 2 S PHENYL 2 THIO ALPHA,BETA DEXTRO GLUCOPYRANOSE; LEWIS ACID; METHYL 2 [(BENZYLOXYCARBONYL)AMINO] 3 O (2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO GLUCOPYRANOSYL)PROPANOATE; METHYL 2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO GLUCOPYRANOSYL(1-3) 2 O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO GLUCOPYRANOSYL(1-4) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3,4,6 TETRA O BENZYL ALPHA,BETA DEXTRO GLUCOPYRANOSYL(1-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3,4,6 TETRA O BENZYL DEXTRO GLUCOPYRANOSYL(1-3) 2 O BENZYL 4,6 O BENZYLIDENE BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3,4,6 TETRA O BENZYL DEXTRO GLUCOPYRANOSYL(1-4) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; STOICHIOMETRY;

CARBAMATES; CARBOHYDRATES; CATALYSIS; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77949568237     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2010.01.011     Document Type: Article

References (53)

1. Seeberger P.H., and Werz D.B. Nature 446 (2007) 1046-1051
2. In: Demchenko A.V. (Ed). Handbook of Chemical Glycosylation (2008), Wiley-VCH, Weinheim
3. Boons G.J. Tetrahedron 52 (1996) 1095-1121
4. Danishefsky S.J., and Bilodeau M.T. Angew. Chem., Int. Ed. 35 (1996) 1380-1419
5. Schmidt R.R., and Kinzy W. Adv. Carbohydr. Chem. Biochem. 50 (1994) 21-123
6. Toshima K., and Tatsuta K. Chem. Rev. 93 (1993) 1503-1531
7. Sinaÿ P. Pure Appl. Chem. 63 (1991) 519-528
8. Kunz H., and Zimmer J. Tetrahedron Lett. 34 (1993) 2907-2910
9. Prata C., Mora N., Lacombe J.-M., Maurizis J.C., and Pucci B. Tetrahedron Lett. 38 (1997) 8859-8862
10. Hinklin R.J., and Kiessling L.L. J. Am. Chem. Soc. 123 (2001) 3379-3380
11. Knoben H.-P., Schlueter U., and Redlich H. Carbohydr. Res. 339 (2004) 2821-2833
12. Jayakanthan K., and Vankar Y.D. Carbohydr. Res. 340 (2005) 2688-2692
13. Matsuo J., Shirahata T., and Ōmura S. Tetrahedron Lett. 47 (2006) 267-271
14. Hashimoto S., Hayashi M., and Noyori R. Tetrahedron Lett. 25 (1984) 1379-1382
15. Nagai H., Sasaki K., Matsumura S., and Toshima K. Carbohydr. Res. 340 (2005) 337-353
16. Nakarahra Y., and Ogawa T. Carbohydr. Res. 200 (1990) 363-375
17. Jona H., Mandai H., Chavasiri W., Takeuchi K., and Mukaiyama T. Bull. Chem. Soc. Jpn. 75 (2002) 291-309
18. Toshima K., Kasumi K., and Matsumura S. Synlett (1998) 643-645
19. Kreuzer M., and Thiem J. Carbohydr. Res. 149 (1986) 347-361
20. Inaba S., Yamada M., Yoshino T., and Ishido Y. J. Am. Chem. Soc. 95 (1973) 2062-2063
21. Ishido Y., Inaba S., Matsuno A., Yoshino T., and Umezawa H. J. Chem. Soc., Perkin Trans. 1 (1977) 1382-1390
22. Ishido Y., Inaba S., Komura H., and Matsuno A. J. Chem. Soc., Chem. Commun. (1977) 90-91
23. Garcia B.A., and Gin D.Y. J. Am. Chem. Soc. 122 (2000) 4269-4279 and references cited therein
24. Umemura K., Matsuyama H., Kobayashi M., and Kamigata N. Bull. Chem. Soc. Jpn. 62 (1989) 3026-3028
25. Chiba H., Funasaka S., and Mukaiyama T. Bull. Chem. Soc. Jpn. 76 (2003) 1629-1644
26. Chhabra S.R., Mahajan A., and Chan W.C. J. Org. Chem. 67 (2002) 4017-4029
27. Grayson E.J., Ward S.J., Hall A.L., Rendle P.M., Gamblin D.P., Batsanov A.S., and Davis B.G. J. Org. Chem. 70 (2005) 9740-9754
28. Motawia M.S., Olsen C.E., Denyer K., Smith A.M., and Moller B.L. Carbohydr. Res. 330 (2001) 309-318
29. Hu Y.-J., Dominique R., Das S.K., and Roy R. Can. J. Chem. 78 (2000) 838-845
30. Oshitari T., Tomita M., and Kobayashi S. Tetrahedron Lett. 35 (1994) 6493-6494
31. Chen M.-Y., Patkar L.N., Lu K.-C., Lee A.S.-Y., and Lin C.-C. Tetrahedron 60 (2004) 11465-11475
32. Crich D., and Sun S. Tetrahedron 54 (1998) 8321-8348
33. Wuiff G., and Wichelhaus J. Chem. Ber. 112 (1979) 2847-2853
34. Ōmura S., Tanaka Y., Nakagawa A., Iwai Y., Inoue M., and Tanaka H. J. Antibiot. 35 (1982) 256-257
35. Omura S., Nakagawa A., and Tanaka Y. J. Org. Chem. 47 (1982) 5413-5415
36. Omura S., Tanaka Y., Takahashi Y., Chia I., Inoue M., and Iwai Y. J. Antibiot. 37 (1984) 1572-1578
37. Hirose T., Sunazuka T., Yamamoto D., Mouri M., Hagiwara Y., Matsumaru T., Kaji E., and Omura S. Tetrahedron Lett. 48 (2006) 413-416
38. Roush W.R., Sebesta D.P., and Bennett C.E. Tetrahedron 53 (1997) 8825-8836
39. Roush W.R., Sebesta D.P., and James R.A. Tetrahedron 53 (1997) 8837-8852
40. Roush W.R., Briner K., Kesler B.S., Murphy M., and Gustin D.J. J. Org. Chem. 61 (1996) 6098-6099
41. Roush W.R., Hartz R.A., and Gustin D.J. J. Am. Chem. Soc. 121 (1999) 1990-1991
42. Garegg P.J., and Hultberg H. Carbohydr. Res. 93 (1981) C10
43. Garcia B.A., and Gin D.Y. J. Am. Chem. Soc. 122 (2000) 4269-4279
44. Kim W.-S., Hosono S., Sasai H., and Shibasaki M. Heterocycles 42 (1996) 795-809
45. Fukase K., Hasuoka A., Kinoshita I., Aoki Y., and Kusumoto S. Tetrahedron 51 (1995) 4923
46. Koide K., Ohno M., and Kobayashi S. Tetrahedron Lett. 48 (1991) 7065-7068
47. Wang C.-C., Lee J.-C., Luo S.-Y., Kulkarni S.S., Huang Y.-W., Lee C.-C., Chang K.-L., and Hung S.-C. Nature 446 (2007) 896-899
48. Dasgupta F., and Garegg P. Synthesis (1994) 1121-1123
49. Boons G.J., Castle G.H., Clase J.A., Grice P., Ley S.V., and Pinel C. Synlett (1993) 913-914
50. Dasgupta F., and Garegg P.J. Carbohydr. Res. 177 (1988) C13
51. Vankayalapati H., Singh G., and Tranoy I. Tetrahedron: Asymmetry 12 (2001) 1371-1381
52. Uchiro H., Kurusu N., and Mukaiyama T. Isr. J. Chem 37 (1997) 87-96
53. Uchiro H., Miyazaki K., and Mukaiyama T. Chem. Lett. (1997) 403-404