A General Synthesis of Diterminal Diamnodideoxyalditols and 1-Amino-1-deoxyalditols Using Trimethylmsilyl Protecting Groups

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Abstract
General syntheses of diterminal diaminodideoxyalditols and 1-amino-1-deoxyalditols from aldoses are described. Borane-THF reduction of O-trimethylsilylaldaramides, followed by methanolic HC1 workup, leads to diaminodideoxyalditol dihydrochlorides. Similar treatment of O-trimethylsilylaldonamides yields aminoalditol hydrochlorides. The general reaction sequence was used to synthesize six diaminoalditols and five monoaminoalditols. The method is generally applicable to both classes of title aminoalditols and is independent of the chain length and stereochemistry of the starting aldose.