An improved route to 1,2-dideoxy-β-1-phenyl-D-ribofuranose

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 24, 1998, Pages 3465-3468

  Wichai, Uthai ^a   Woski, Stephen A ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIDEOXY BETA 1 PHENYL DEXTRO RIBOFURANOSE; 2 DEOXYRIBOSE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

DEOXYRIBOSE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 0032534815     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00632-5     Document Type: Article

References (16)

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6. (c) Chaudhuri, N. C.; Ren, R. X.-F.; Kool, E. T. Synlett 1997, 341.
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11. 6. U. Wichai and S. A. Woski, unpublished results.
12. 7. Deriaz, R. E.; Overend, W. G.; Stacey, M.; Teece, E. G.; Wiggins, L. F. J. Chem. Soc. 1949, 1879.
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14. 3): δ 142.3, 128.2, 127.3, 126.0, 88.0, 80.0, 74.4, 63.8, 44.2, 25.9, 25.8, 18.3, 18.0, 4.7, 4.6, 3.9.
15. f = 0.51) afforded 0.514 g of 4 as pale-yellow oil (43 % from 3).
16. 1H NMR spectrum of this material matched that reported by Millican and coworkers (Ref. 1). These workers unequivocally confirmed the β anomeric stereochemistry of their immediate synthetic precursor to 1 (the 3,5-di-O-toluoyl derivative) by X-ray crystallography (Gunning, J.; Neidle, S.; Millican, T. A.; Eaton, M. A. W.; Mock, G. A.; Mann, J. Acta Cryst. 1985, C41, 720.).