Synthesis of bis(1,3-dihydroxy-isopropyl)amine by reductive amination of dihydroxyacetone: Open chain equivalent of DMDP and a potential AB(4) dendritic monomer

Journal article

Reductive amination of dihydroxyacetone by ammonium salts with sodium cyanoborohydride gives bis(1,3-dihydroxy-isopropyl)amine [BDI] in good yield and high purity. BDI and its diacetonide are hindered nucleophiles but may be further reductively alkylated to form N-alkyl derivatives. BDI is an open chain equivalent of DMDP [2,5-dideoxy-2,5-imino-D-mannitol] but neither BDI nor its N-alkyl derivatives show inhibition of any glycosidase or transferase assayed. BDI may provide an example of an AB4 dendritic monomer.

Authors: Scott, D; Krulle, T; Finn, M; Nash, R; Winters, A

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 40
• Issue: 42
• Pages: 7581-7584
• Publication date: 1999-10-15
• DOI: 10.1016/S0040-4039(99)01611-1
• ISSN: 0040-4039
• Language: English