Determination of the absolute stereochemistry at the C16 orthoester of everninomicin antibiotics; a novel acid-catalyzed isomerization of orthoesters

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 7989-7992

  Ganguly, Ashit K ^a   McCormick, Jinping L ^a   Chan, Tze Ming ^a   Saksena, Anil K ^a   Das, Pradip R ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; EVERNINOMICIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG STRUCTURE; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0030729373     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10178-2     Document Type: Article

References (10)

1. Girijavallabhan, V.M.; Ganguly, A.K. Kirk-Othmer Encyclopedia of Chemical Technology 4th Ed., John Wiley & Son, 1992; Vol. No. 3, pp 259-266.
2. Ganguly A.K., Saksena A.K. J. Antibiotics. 28:1975;707.
3. Ganguly A.K., Szmulewicz S. J. Antibiotics. 28:1975;710.
4. Ganguly A.K., Sarre O.Z., Greeves D., Morton J. J. Am. Chem. Soc. 97:1975;1982.
5. Ganguly A.K., Pramanik B., Chan T.M., Sarre O.Z., Liu Y.-T., Morton J., Girijavallabhan V. Heterocycles. 28:1989;83.
6. Everninomicins are members of a family of oligosaccharide antibiotics, also referred to as orthosomycins. For a review, see Wright, D.E. Tetrahedron 1979, 35, 1207.
7. Ganguly, A.K.; Sarre, O.Z.; McPhail, A.T.; Miller, R. J. Chem. Soc. Chem. Com. 1979, 22.
8. Beau, J.-M.; Jaurand, G.; Esnault, J.; Sinay, P. Tetrahedron Lett. 1987, 1105.
9. Chan T.-M., Osterman R.M., Morton J.B., Ganguly A.K. Magn. Res. Chem. 35(8):1997;529.
10. 2) gave 2 (67 mg, white solid) and 3 (224 mg, white solid).