Pentofuranoside synthesis

In 2008, the research group of Singh reported the synthesis of imidazohum-based ionic liquids in which the chiral moiety was constituted of a pentofuranoside unit [79]. The 2,3,5-tri-O-benzyl-D-arabinofuranose 45, easily prepared from commercial D-arabinose in 75% yield following known procedures, was transformed... 

The dihydrofuran derivative 35 was also employed for the synthesis of ethyl 3-amino-3-deoxy-/3-DL-arafiino-pentofuranoside (40b). The synthesis was accomplished27 in three stages. By the action of calcium hypochlorite on 35, a chlorohydrin intennediate was formed which, on treatment with a base, afforded a mixture of the epoxides 37, 38,... 

S. Watanabe, J. Kavai, and M. Bobek, Cyano sugars synthesis by opening of an epoxide ring in pentofuranosides with diethylaluminium cyanide, J. Carbohydr. Chem., 14 (1995) 685-701. 

Bogusiak, J, Szeja, W, Studies on the synthesis of 1,2-cis pentofuranosides from S-glycofuranosyl dithiocarbamates, dithiocarbonates and phosphorodithioates, Carbohydr. Res., 330, 141-144, 2001. 

Synthesis of a hexopyranoside from a pentofuranoside in the way just described constitutes a chain elongation from within, concomitant with introduction of a nitrogen-containing substituent. This principle57 has been successfully applied in the chemical modification of nucleosides. Pursuant to preliminary reports on such modifications by Fox70 and Lichtenthaler71 and their associates, a considerable body of detailed work in that direction has appeared.72-80... 

A sie novo synthesis of C-phenyl pentofuranosides is illustrated briefly in Scheme 27. °° A further phenyl... 

Anhydro-l,4-di-0-benzyl-L-threitol on reaction with allylmagnesium bromide, osmium tetroxide, sodium periodate then HCl affords methyl 3-C-(benzyloxymethyl)-2,3-dideoxy-L-r/ireo-pentofuranoside as a useful intermediate for the synthesis of 2 3 -dideoxy-3 -C-(hydroxymethyl)-4 -thionucleosides. In an alternative route to such nucleosides the intermediate branched-sugar 50 was prepared in which the hydroxymethyl group was introduced into the 3-position by a light-induced addition of methanol to 6-O-rerr-butyldimethylsilyl-D-g/yceru-pent-2-eno-1,4-lactone (see Vol. 26, p. 242, ref. 159). ... 

An asymmetric synthesis of ethyl 2,3-dideoxy-4-C-methyl-3-C-methylene-D-g/ycero-pentofuranosides has been described. Thus, regioselective cyclization of the chiral acetal 62 (derived from 2,3-dimethyl-2-butenal) under acidic conditions. 

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