Pentitol, 2-deoxy-erythro

Generally speaking, the phosphorylated deoxysugars undergo the usual reactions of carbohydrates without complication. For instance, both 2-deoxy D-ribose 5-phosphate (52, 59) and 2-deoxy D-xylose 5-phosphate (2) can be reduced to the corresponding 2-deoxy d-erythro- (48) and 2-deoxy D-threo-pentitol 5-phosphates (49). 2-deoxy ribose 5-phosphate has also been oxidized (52) to the corresponding phosphorylated acid (50). 

Biological dehydrogenation of 2-deoxy-D-erythro-pentitol (6) by Glucono-bacter oxydans has been used to prepare 4-deoxy-L-g /ycero-pentulose (7), characterized by m.s. of its tri(trimethylsilyl) derivative. ... 

Cyclization by Displacement of Leaving Groups in Carbohydrate Substrates by Amines. The synthesis of l,2,4-trideoxy-l,4-imino-D-erythro-pentitol (31) has been achieved in eight steps, in 42% overall yield, from 2,5-di-O-p-tol-uenesulfonyl-D-ribono-1,4-lactone according to Scheme 7. The correct stereochemistry in the product was achieved by epimerization at C-4 in a 5-0-tosylated 2-deoxy lactone intermediate base action on the lactone produced a 4,5-epoxide of an open-chain carboxylate derivative which subsequently ring-closed by intramolecular attack of the carboxylate anion on the epoxide to produce the diastereomeric lactone. ... 

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