Efficient methodology for the synthesis of 2-C-branched glyco-amino acids by ring opening of 1,2-cyclopropanecarboxylated sugars

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1777-1779

  Sridhar, Perali Ramu ^a   Ashalu, K Chinna ^a   Chandrasekaran, S ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOXYL GROUP; CYCLOPROPANE; SUGAR;

ARTICLE; CARBOXYLATION; CHEMICAL REACTION; METHODOLOGY; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

AMINO ACIDS; CARBOHYDRATES; CYCLOPROPANES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 2942628414     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049467v     Document Type: Article

References (16)

1. For a recent review on the preparation and ring opening of cyclopropanated carbohydrates, see: Cousins, G. S.; Hoberg. J. O. Chem. Soc. Rev. 2000, 29, 165.
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9. (b) Beyer, J.; Skaanderup, R.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 9575.
10. A glyco-amino acid (GAA) is a saccharide attached to a single amino acid by any kind of covalent bond. McDevitt, J. P., Jr.; Lansbury, P. T. J. Am. Chem. Soc. 1996, 118, 3818.
11. 13C NMR spectra of compound 3 showed only 13 lines in addition to the aromatic signals.
12. Sridhar, P. R.; Prabhu, K. R.; Chandrasekaran, S. J. Org. Chem. 2003, 68, 5261.
13. The high diastereoselectivity at the anomeric center may be attributed to the neighboring group (COOMe) participation.
14. 1H NMR spectroscopy.
15. The configuration of all GAA derivatives were assigned on the basis of the coupling constants and also the structure of compound 22.
16. 2 = 0.132 (all data).