Mild oxidation of cytidine-sialic acid phosphite derivatives using dimethyldioxirane

Tetrahedron Letters

Volumn 40, Issue 1, 1999, Pages 1-4

  Chappell, Mark D ^a   Halcomb, Randall L ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

CMP Neu5Ac; Dimethyldioxirane

Indexed keywords

CYTIDINE; DIMETHYLDIOXIRANE; ETHYLENE OXIDE DERIVATIVE; PHOSPHITE; SIALIC ACID; SODIUM PEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CELL ADHESION; CELL FUNCTION; DERIVATIZATION; DRUG SYNTHESIS; GEL CHROMATOGRAPHY; GLYCOSYLATION; HYDROLYSIS; NONHUMAN; OXIDATION; TARGET CELL;

EID: 0032889289     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)80002-6     Document Type: Article

References (13)

1. (a) Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785.
2. (b) Varki, A. Glycobiology 1993, 3, 97.
3. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683.
4. Chappell, M. D.; Halcomb, R. L. J. Am. Chem. Soc. 1997, 119, 3393.
5. (a) Unverzaght, C.; Kunz, H.; Paulson, J. C. J. Am. Chem. Soc. 1990, 112, 9308.
6. (b) Ichikawa, Y.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 4698.
7. Liu, J. L.-C.; Shen, G.-J.; Ichikawa, Y.; Rutan, J. F.; Zapata, G.; Vann, W. F.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 3901.
8. Chappell, M. D., Halcomb, R. L. Tetrahedron 1997, 53, 11109.
9. (a) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811.
10. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187.
11. 3) δ -4.54, -4.60.
12. Dioxirane solutions were prepared following the small scale precedure and titrated using the phenyl methyl sulfide method. Adam, W.; Chan, Y.-Y.; Cremer, D.; Gauss, J.; Scheutzow, D.; Schindler, M. J. Org. Chem. 1987, 52, 2800.
13. Treatment of 5 with DMD at room temperature and concentration on the rotorary evaporator led to some decomposition of the phosphate 9.