论文信息 - Synthesis of 1-O-R-5-deoxy-?-D-ribofuranosides with (CH3)2As and (CH3)2As?O as substituents at the 5-position and a methyl or 2?,3?-dihydroxypropyl group as the aglycone in the 1-position

Synthesis of 1-O-R-5-deoxy-?-D-ribofuranosides with (CH3)2As and (CH3)2As?O as substituents at the 5-position and a methyl or 2?,3?-dihydroxypropyl group as the aglycone in the 1-position

Six arsenic-containing β-D-ribofuranosides, including the naturally occurring (2'R)-dimethyl[1-O-(2',3'-dihydroxypropyl)-5-deoxy-β -D-ribofuranos-5-yl]arsine oxide, were prepared in multi-step reactions from D-ribose and tetramethyldiarsine. The synthetic procedure uses the early substitution of the hydroxy group with bromine at C5, subsequent attachment of a chiral three-carbon aglycone at C1, and final delivery of arsenic at C5. The synthesis provides a viable route for the preparation of multigram quantities of the natural product

K. Irgolic | Jinggao Liu | D. H. O'brien

[1] J. Edmonds,et al. Synthesis, NMR spectra and chromatographic properties of five trimethylarsonioribosides , 1994 .

[2] K. Reimer,et al. Arsenic speciation in the environment , 1989 .

[3] D. Mcadam,et al. The Synthesis of (R)-2',3'-Dihydroxypropyl 5-Deoxy-5-Dimethylarsinyl-β-D-Riboside, a Naturally Occurring Arsenic-Containing Carbohydrate , 1987 .

[4] A. Serianni,et al. [13C]-Enriched tetroses and tetrofuranosides: an evaluation of the relationship between NMR parameters and furanosyl ring conformation , 1984 .

[5] H. Eibl. An improved method for the preparation of 1,2-isopropylidene-SN-glycerol , 1981 .

[6] J. Baldwin,et al. Synthesis of (R)- and (S)-epichlorohydrin , 1978 .

[7] J. Baldwin,et al. Synthesis of r epi chlorohydrin and s epi chlorohydrin , 1978 .

[8] L. Lerner. Enantiomeric forms of 9-(5-deoxy-beta-erythro-pent-4-enofuranosyl)adenine and a new preparation of 5-deoxy-D-lyxose. , 1977, Carbohydrate research.

[9] A. Rosenthal. Chemical synthesis of phospholipids and analogues of phospholipids containing carbon-phosphorus bonds. , 1975, Methods in enzymology.

[10] S. Hanessian,et al. Procedures for the direct replacement of primary hydroxyl groups in carbohydrates by halogen , 1972 .

[11] T. D. Inch. Nuclear Magnetic Resonance Spectroscopy in the Study of Carbohydrates and Related Compounds , 1969 .

[12] A. Haug,et al. Synthesis of 1-O-beta-D-Galactofuranosyl-D-glycerol. , 1967 .