647376-91-8

Upstream product

• 76-83-5 trityl chloride 
• 647376-90-7 (1S,2S)-(+)-2-tert-butoxycarbonylamino-1-(4-nitrophenyl)-1,3-propanediol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 

Downstream Products

• 1884-88-4 (1S,2S)-2-amino-1-(4-nitrophenyl)-3-(triphenylmethoxy)propan-1-ol 

Relevant academic research and scientific papers

Synthetic studies on d-biotin. Part 7: A practical asymmetric total synthesis of d-biotin via enantioselective reduction of meso-cyclic imide catalyzed by oxazborolidine

A novel and convenient method for the stereoselective synthesis of d-biotin 1 starting from the commercially available cis-1,3-dibenzyl-2- imidazolidone-4,5-dicarboxylic acid 2 has been developed. The key features of this synthesis include the enantioselective reduction of a meso-cyclic imide, mediated by a chiral oxazborolidine catalyst, derived from (1S,2S)-(+)-threo-1- (4-nitrophenyl)-2-amino-1,3-propanediol and the direct introduction of a C 5 side chain to the (3aS,6aR)-thiolactone through a modified di-Grignard reaction. Enantioselectivities of 98% in the oxazborolidine- catalyzed asymmetric reduction process have been achieved.