Process for the production of DATH and intermediates thereof

A method of producing 6,6′-diamino-6,6′-dideoxy-trehalose or a salt thereof, the method comprising:

• (1) optionally providing a D-trehalose derivative, comprising protecting and/or replacing one or more primary and/or secondary hydroxyl groups of D-trehalose to provide the D-trehalose derivative;
• (2) protecting one or more primary hydroxyl groups and one or more secondary hydroxyl groups of the D-trehalose or the D-trehalose derivative to provide intermediate IA or replacing the primary hydroxyl groups of the D-trehalose or the D-trehalose derivative with iodides to provide an intermediate IB;
• (3) replacing the primary hydroxyl protected groups of intermediate IA with protected amines to provide intermediate 2 or with azides to provide intermediate 2B;
• or (a) protecting secondary hydroxyl groups at carbons 2, 3, and/or 4 of the intermediate IB to provide intermediate IB-1, and (b) replacing the iodides of intermediate IB-1 with protected amines to provide intermediate 2 or with azides to provide intermediate 2B;
• (4) converting the azides, if present, of intermediate 2B into protected amines to provide intermediate 2;
• and
• (5) converting the intermediate 2 to 6,6′-diamino-6,6′-dideoxy-trehalose or a salt thereof;
• wherein the method excludes trityl, tosyl, or trityl and tosyl protecting groups.