Boat conformations - Synthesis, NMR spectroscopy, and molecular dynamics of methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-α-D-altropyranoside derivatives

Carbohydrate Research

Volumn 331, Issue 4, 2001, Pages 461-467

  Coxon, Bruce ^a,b   Reynolds, Robert C ^b  

^a EUNICE KENNEDY SHRIVER NATIONAL INSTITUTE OF CHILD HEALTH AND HUMAN DEVELOPMENT   (United States)

^b NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

1H NMR spectroscopy; Altropyranoside; Boat conformations; Molecular dynamics; Phthalimido derivative; Simulated annealing; Skew boat conformations; Vicinal coupling constants

Indexed keywords

CONFORMATIONS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

BOAT CONFORMATIONS;

CARBOHYDRATES;

METHYL 2,3 ANHYDRO 4,6 O BENZYLIDENE ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 4,6 O BENZYLIDENE 3 DEOXY 3 PHTHALIMIDO ALPHA DEXTRO ALTROPYRANOSIDE DERIVATIVE; PHTHALIMIDE DERIVATIVE; PYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS;

CARBOHYDRATE CONFORMATION; DEOXY SUGARS; MOTION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHTHALIMIDES;

EID: 0035938023     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(01)00036-2     Document Type: Article

References (17)

1. Coxon B. Carbohydr. Res. 13:1970;321-330.
2. Coxon B. Carbohydr. Res. 322:1999;120-127.
3. Coxon B. Carbohydr. Res. 329:2000;131-139.
4. Coxon B. Tetrahedron. 21:1965;3481-3503.
5. Lee, J. B.; Scanlon, B. J. Chem. Soc., Chem. Commun. 1969, 955-956.
6. Picq D., Carret G., Anker D. Carbohydr. Res. 149:1986;458-463.
7. Lin G.H.-Y., Sundaralingam M., Jackobs J. Carbohydr. Res. 29:1973;439-449.
8. Bissember B.B., Wightman R.H. Carbohydr. Res. 91:1981;89-92.
9. Miethchen; R., Rentsch; D., Michalik; M. Liebigs Ann. Chem. 1994, 219-222.
10. Kovarikova R., Ledvina M., Saman D. Collect. Czech. Chem. Commun. 64:1999;673-684.
11. Homans S.W., Forster M. Glycobiology. 2:1992;143-151.
12. Coxon B., Reynolds R.C. Carbohydr. Res. 110:1982;43-54.
13. Dauber-Osguthorpe P., Roberts V.A., Osguthorpe D.J., Wolff J., Genest M., Hagler A.T. Proteins. 4:1988;31-47.
14. Pérez S., Imberty A., Engelsen S.B., Gruza J., Mazeau K., Jimenez-Barbero J., Poveda A., Espinosa J.-F., van Eyck B.P., Johnson G., French A.D., Kouwijzer M.L.C.E., Grootenuis P.D.J., Bernardi A., Raimondi L., Senderowitz H., Durier V., Vergoten G., Rasmussen K. Carbohydr. Res. 314:1998;141-155.
15. Goldberg, R. personal communication.
16. Robertson; G. J., Griffith; C.F. J. Chem. Soc. 1935, 1193-1201.
17. Myers W.H., Robertson G.J. J. Am. Chem. Soc. 65:1943;8-11.