Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors

Organic Letters

Volumn 6, Issue 6, 2004, Pages 973-975

  Dabideen, Darrin R ^a   Gervay Hague, Jacquelyn ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; BETA THIOMANNOSIDE DERIVATIVE; GALACTOSYLIODIDE; GLUCOSYLIODIDE; GLYCOSYLIODIDE DERIVATIVE; IODINE DERIVATIVE; MANNOSIDE; MANNOSYLIODIDE; PROPYLENE OXIDE; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; RING OPENING;

CYCLOPARAFFINS; EPOXY COMPOUNDS; ETHERS, CYCLIC; GLYCOCONJUGATES; GLYCOSIDES; GLYCOSYLATION; MOLECULAR STRUCTURE; TRIMETHYLSILYL COMPOUNDS;

EID: 1642446503     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049966w     Document Type: Article

References (19)

1. (a) Lam, S. N.; Gervay-Hague, J. Org. Lett. 2002, 4, 2039-2042.
2. (b) Lam, S. N.; Gervay-Hague, J. Carbohydr. Res. 2002, 337, 1953-1965.
3. (c) Bhat, A. S.; Gervay-Hague, J. Org. Lett. 2001, 3, 2081-2084.
4. (d) Gervay, J. Organic Synthesis: Theory and Applications; JAI Press: Greenwich, 1998; pp 121-153.
5. (e) Hadd, M. J.; Gervay, J. Carbohydr. Res. 1999, 320, 61-69.
6. (f) Gervay, J.; Hadd, M. J. J. Org. Chem. 1997, 62, 6961-6967.
7. Hadd, M. J. Ph.D. Thesis, University of Arizona, Tucson, AZ, 1998.
8. Fraser-Reid, B.; Konradsson, P.; Mootoo, D. R.; Udodong, U. J. Chem. Soc., Chem. Commun. 1988, 823-825.
9. Thiem, J.; Meyers, B. Chem. Ber. 1980, 113, 3075-85.
10. Vila, A.; Mosquera, R. A. Tetrahedron 2001, 57, 9415-9422.
11. Gridley, J. J.; Osborn H. M. I. J. Chem. Soc., Perkin Trans. 1 2000, 1471-1491.
12. (a) Barresi, F.; Hindsgaul, O. Front. Nat. Prod. Res. 1996, 1, 251-276.
13. (b) Stork, G.; LeClair, J. J. J. Am. Chem. Soc. 1996, 118, 247-248.
14. (a) Hodosi, G.; Kovác, P. J. Am. Chem. Soc. 1997, 118, 22335-2336.
15. (b) Crich, D.; Sun, S. J. Org. Chem. 1997, 62, 1198-99.
16. Lam, S. N.; Gervay-Hague, J. Org. Lett. 2003, 22, 4219-22.
17. Gronert, S.; Lee, J. M. J. Org. Chem. 1995, 60, 6731-36.
18. C,H coupling constant data as per: Bock, K.; Lundt, I.; Pedersen, C. Tetrahedron Lett. 1973, 14, 1037-1040.
19. For examples of conformationally biased β-selective thioglycosidations, see: Crich, D.; Li, H. J. Org. Chem. 2000, 65, 801-805 and references therein.