Hexono-1,4-lactone preparation

E. Ayadi, S. Czemecki, and J. Xie, Convenient preparation of perbenzylated 2-azido and 2-iV-acetylamino-2-deoxy-D-hexono-1,5-lactones by oxidation of the corresponding lactols,. /. Carbohydr. Chem., 15 (1996) 191-199. 

There has been a continuing interest in syntheses of 3-amino-2,3,6-trideoxy-hexoses such as daunosamine (9), acosamine (10), etc. In an interesting paper by Fronza et the two sugars have been synthesized from the non-carbohydrate compound (11), which was obtained in 25-30% yield from the incubation of cinnamaldehyde v th acetaldehyde in the presence of bakers yeast (Scheme 2). The crucial amino-lactone (12) was also synthesized from L-threonine. The same authors have also completed their synthesis of A-benzoyl-L-ristosamine (3-benzamido-2,3,6-trideoxy-L /6o-hexose) from 3-benzamido-2,3,6-trideoxy-L-xy/o-hexono-1,5-lactone (Vol. 13, p. 79). An alternative synthesis of methyl A-acetyl-a-L-acosaminide (13) has been described by reduction of the appropriate acetylated oxime by diborane. The thioglycoside (14) was also prepared. ... 

The D-gluco-diazirine derivative (45) and its D-manno- and D-galacto-analogues have been prepared from the corresponding hexono-1,5-lactone oximes, and shown to be stable at low temperatures (Scheme 9). They are precursors of... 

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