Carbohydrate Research p. 19 - 24 (1986)
Update date:2022-08-11
Topics:
Tiwari, Kamal N.
Dhawale, Motiram R.
Szarek, Walter A.
Hay, George W.
Kropinski, Andrew M. B.
2-Deoxy-D-arabino-hexitol (6) was obtained by borohydride reduction of 2-deoxy-D-arabino-hexose (5).The synthesis of 5, starting from 2,3:4,5-di-O-isopropylidene-D-arabinitol (1), was achieved by one-carbon chain-elongation involving formylation of the Grignard reagent derived from 1-bromo-1-deoxy-2,3:4,5-di-O-isopropylidene-D-arabinitol (2), using lithium formate, followed by hydrolytic removal of the isopropylidene groups.Immobilized cells of Gluconobacter oxydans (ATCC) 15178) selectively oxidized 6 to give 5-deoxy-D-threo-hexulose (7) in 65percent yield (-9percent overall yield from 1).
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