Reduction products and bromodeoxy derivatives of dehydro-L-ascorbic acid 2- [phenylhydrazone]

ABSTRACT

Dehydro-L-ascorbic acid 2-[phenylhydrazone] [I] was reduced by sodium borohydride to 3,6-anhydro-L-xylo-2-hexulosono-1,4-lactone-2- [phenylhydrazone] [II] which gave a mono-O-acetyl- and mono-O-benzoyl derivatives III and IV, respectively. Treatment of I with HBr/AcOH gave the 5,6-dibromo-5,6-dideoxy derivatives VI that gave a number of condensation products VII-XI, while treatment of I with methylhydrazine gave 1-methyl-3-[2,3-dibromo-2,3-dideoxy-L-threo- glycerol-1-yl]- 4,5-pyrazolinedione-4-[phenylhydrazone] [XII]