Hexose 3-benzamido-2,3,6-trideoxy

Fuganti and co-workers used 2R 3R-tartaric acid for the synthesis of 3-benzamido-2,3,6-trideoxy-L-xy/o-hexose (393). The acid was converted according to a known procedure into 2,3-0-isopropylidene-4-0-p-toluenesulfonyl-L-threitol (388). Reduction of 388 with lithium aluminum hydride gave 4-deoxy-... 

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. ... 

Acetamido-2,3,6-trideoxy-4-0-methyl-L-araZ)in -hexose, A-458 2-[3-Acetamido-2,4,6-triiodo-5-(A-methylacetamido)benzamido]-2-deoxy-D-... 

Benzamido-2,3,6-trideoxy-D-/yxo-hexose, A-461 3-Benzamido-2,3,6-trideoxy-L-/j xo -hexose, A-461 3-Benzamido-2,3,6-trideoxy-L-W/)o -hexose, A-462 Benzyl 3-amino-3-deoxy-p-D-altropyranoside, A-165 Benzyl 2,3-diacetamido-4-0-benzyl-2,3-dideoxy-a-D-xylopyranoside, D-462... 

Dideoxy-3-(L-glyceroylamino)-D-glua>se, A-381 3",4 -Dideoxykanamycin B, D-625 3",4 -Dideoxy-3"-A-methylkanamycm B, D-625 3-(Dimethylamino)-2,3,6-trideoxy-ara6 io-hexose t>-form, D-726 3-(Dimethylamino)-2,3,6-trideoxy-/yxo-hexose L-form, D-727 Ethyl 3-benzamido-4-0-benzoyl-2,3,6-trideoxy-3-C-methyl-a-L-/ xro-... 

In both syntheses, epimerlzatlon at C-4 was effected by an oxidation -reduction sequence. Details have been published on the syntheses of the four configurational isomers of 2,3,6-trideoxy-3-C-methyl-3-benzamido-L-hexose from a yeast-produced a-methylcinnamaldehyde-... 

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