79875-95-9Relevant articles and documents
C-Nucleoside Studies. Part 13. A New Synthesis of 2,3,5-Tri-O-benzyl-α(and β)-D-ribofuranosylethyne Involving Benzyloxy Participation, and a Synthesis of α-Showdomycin
Aslani-Shotorbani, Gaffar,Buchanan, J. Grant,Edgar, Alan R.,Shanks, Colin T.,Williams, Gavin C.
, p. 2267 - 2272 (2007/10/02)
2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60 deg C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group.The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-benzyl-1-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its O-5 oxyanion.Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-α (and β)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose.A synthesis of 2-α-D-ribofuranosylmaleimide, the α-isomer showdomycin, from (20) is described.
