612065-80-2

Upstream product

• 7396-44-3 benzyl diethylphosphonoacetate 
• 95484-17-6 4-N-(benzyloxycarbonyl)-butan-2-one 
• 612065-83-5 N-(benzyloxycarbonyl)-4-aminobutanol-2 
• 501-53-1 benzyl chloroformate 
• 34637-22-4 3-[(N-benzyloxycarbonyl)amino]propanol 
• 65564-05-8 3-[(benzyloxycarbonyl)amino]propanal 

Downstream Products

• 612065-81-3 (2S,3R)-5-Benzyloxycarbonylamino-2,3-dihydroxy-3-methyl-pentanoic acid benzyl ester 

Relevant academic research and scientific papers

Studies on the synthesis of (2S,3R)-3-hydroxy-3-methylproline via C 2-N bond formation

A new efficient synthesis of (2S,3R)-3-hydroxy-3-methylproline (3) is reported. During the course of a recent study on the Lewis acid promoted intramolecular opening of an epoxide by a carbamate NH, a highly concerted rearrangement was unexpectedly observed. Further investigations of substrate generality show that δ-carbamate-α,β-epoxide esters commonly underwent similar rearrangements with the aid of Lewis acids. Retrosynthetic analysis of such a C2 - N disconnection can lead to an efficient synthesis of (2S,3R)-3-hydroxy-3-methylproline (3) in high enantio purity. Stereochemistries were established by a Sharpless asymmetric dihydroxylation and a diastereo-selective reductive amination.