A de novo synthesis of ethyl 2-deoxy-L-ribosides

Tetrahedron Letters

Volumn 39, Issue 26, 1998, Pages 4615-4618

  Jung, Michael E ^a   Nichols, Christopher J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYL 2 DEOXYRIBOSE; NUCLEOSIDE; RIBOSE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; EPOXIDATION; PROTEIN STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032565940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00852-1     Document Type: Article

References (61)

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56. 13C NMR data with that for the known methyl 2-deoxy-2-methyl-D-ribopyranoside (Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron: Asymmetry 1996, 7, 779) and furanosides (Arshava, B. M.; Raifel'd, Y. E.; Makin, S. M. J. Org. Chem. USSR 1990, 26, 666 (Zh. Org. Khim. 1990, 26, 778). The structure of the pyranoside is assigned as the β-anomer since treatment of 2-deoxy-D-ribose with methanol and acid is known to form the β-anomer in preference to the α in a 9:1 ratio (Jandu, K. S.; Selwood, D. L. J. Org. Chem. 1995, 60, 5170).
57. 13C NMR data with that for the known methyl 2-deoxy-2-methyl-D-ribopyranoside (Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron: Asymmetry 1996, 7, 779) and furanosides (Arshava, B. M.; Raifel'd, Y. E.; Makin, S. M. J. Org. Chem. USSR 1990, 26, 666 (Zh. Org. Khim. 1990, 26, 778). The structure of the pyranoside is assigned as the β-anomer since treatment of 2-deoxy-D-ribose with methanol and acid is known to form the β-anomer in preference to the α in a 9:1 ratio (Jandu, K. S.; Selwood, D. L. J. Org. Chem. 1995, 60, 5170).
58. 13C NMR data with that for the known methyl 2-deoxy-2-methyl-D-ribopyranoside (Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron: Asymmetry 1996, 7, 779) and furanosides (Arshava, B. M.; Raifel'd, Y. E.; Makin, S. M. J. Org. Chem. USSR 1990, 26, 666 (Zh. Org. Khim. 1990, 26, 778). The structure of the pyranoside is assigned as the β-anomer since treatment of 2-deoxy-D-ribose with methanol and acid is known to form the β-anomer in preference to the α in a 9:1 ratio (Jandu, K. S.; Selwood, D. L. J. Org. Chem. 1995, 60, 5170).
59. 13C NMR data with that for the known methyl 2-deoxy-2-methyl-D-ribopyranoside (Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron: Asymmetry 1996, 7, 779) and furanosides (Arshava, B. M.; Raifel'd, Y. E.; Makin, S. M. J. Org. Chem. USSR 1990, 26, 666 (Zh. Org. Khim. 1990, 26, 778). The structure of the pyranoside is assigned as the β-anomer since treatment of 2-deoxy-D-ribose with methanol and acid is known to form the β-anomer in preference to the α in a 9:1 ratio (Jandu, K. S.; Selwood, D. L. J. Org. Chem. 1995, 60, 5170).
60. 23) Another run under similar conditions with only 2 h at reflux resulted in the same products 2abc in a 2:1:1 ratio.
61. 24) Treatment of the aldehyde 23 under the same conditions using water in place of ethanol resulted in a low yield of a compound whose NMR matched that of natural 2-deoxy-D-ribose and therefore was presumably 1. However, it could not be isolated in good yield by this route.