425622-85-1

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 99113-35-6 ((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester 
• 103127-52-2 ((S)-1-benzylallyl)carbamic acid tert-butyl ester 
• 425622-84-0 ((1S,2R)-1-Benzyl-2,3-bis-benzyloxy-propyl)-carbamic acid tert-butyl ester 
• 425622-83-9 Benzyl-((1S,2R)-1-benzyl-2,3-bis-benzyloxy-propyl)-amine 
• 6921-34-2 benzylmagnesium chloride 
• 1589-82-8 phenylmagnesium bromide 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 220871-52-3 1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane 
• 425622-87-3 methanesulfonic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-propyl ester 

Relevant academic research and scientific papers

Highly convergent stereoselective synthesis of chiral key intermediates in the synthesis of Palinavir from imines derived from L-glyceraldehyde

Imines derived from O-protected (S)-glyceraldehyde are valuable intermediates in the synthesis of different kinds of amino acids. We have developed a highly convergent and stereoselective method to obtain (2S,3S)-N-tert-butoxycarbonyl-1-phenyl-3,4-epoxy-2-butylamine and (2S,4R)-N-tert-butoxycarbonyl-4-hydroxypipecolic acid tert-butylamide, which are key intermediates in the synthesis of Palinavir, that consist in the treatment of the appropriate imine with benzylmagnesium bromide and Danishefsky's diene, respectively, and subsequent transformation of the obtained adducts into the desired compounds. The reaction of N-benzylimine derived from (S)-2,3-di-O-benzylglyceraldehyde with benzylmagnesium bromide is completely diastereoselective at low temperature. Hetero Diels-Alder reaction of imine derived from (S)-2,3-di-O-benzylglyceraldehyde and (R)-N-α-methylbenzylamine is completely diastereoselective at low temperature in the presence of ZnI2.

A convenient synthesis of 1-(S)-[1'-(S)-(t-butyloxycarbonylamino)-2'- phenylethyl]oxirane. A useful building block in the synthesis of HIV protease inhibitors

A new short route to epoxide 6b, a pivotal intermediate for the preparation of hydroxyethylamine dipeptide isosteres has been developed. Opening of the epoxide by anthranilic acid, followed by extensions in the P2/P3-region gave the target compounds which were evaluated as HIV-1 protease inhibitors.