Aminoaldonic acids

Amino- (48, 50, 51) and diaminoalditols (37-44), aminoaldonic acids (45-47, 49), diaminoanhydroalditols, and some others amino-derivative of sugars (52-58) have been extensively used in the preparation of polyamides, polyurethanes and polynireas. 

This section deals with acids, that are formally modified aldonic acids, such as keto, deoxy, and branched-chain acids (including the so-called saccharinic acids). The aminoaldonic acids, which are oxidation products of amino sugars, and, in particular, the important nonulosaminic acids (neuraminic acids) and muramic acid, are not discussed here. The formation of saccharinic acids by the treatment of sugars with alkali, and the mechanisms involved, are likewise outside the scope of this chapter. 

The aminohomologation of (/ )-24 via nitronate 53 can use the addition of 2-lithiofuran instead of 2-lithiothiazole. The furyl moiety can then be oxidized to the corresponding 2-aminoaldonic acids [67b]. Alternatively, the nucleophilic addition of alkoxy-methyllithium derivatives to nitrones of type 53 are either syn or anti selective in the absence or the presence of Et2AlCl, respectively. The adducts thus obtained were converted into C-4 building blocks and (3-hydroxy-a-aminoacids [67c]. 

Cleavage of the acetonide group of the acyclic a-aminoaldonic acid derived 57 with an acid resin, followed by hydrogenolysis, affords 2,S-dideoxy-2,5-imino-D-maniutol. ... 

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