129778-81-0

Upstream product

• 72155-45-4 Boc-L-phenylalaninal 
• 762-72-1 allyl-trimethyl-silane 
• 3182-95-4 L-Phenylalaninol 
• 160002-06-2 (S)-tert-butyl 3-oxo-1-phenylhex-5-en-2-ylcarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 250668-93-0 (2S)-3-phenyl-2-[N-(tert-butoxycarbonyl)amino]propanoyldimethylphenylsilane 
• 34101-07-0 (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-imidazol-1-yl-3-phenylpropan-1-one 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 63-91-2 L-phenylalanine 
• 1730-25-2 allylmagnesium bromide 
• 250668-95-2 syn-(2S,3R)-2-[N-(tert-butoxycarbonyl)amino]-3-dimethylphenylsilyl-1-phenyl-5-hexen-3-ol 
• 24850-33-7 allyltributylstanane 
• 106-95-6 allyl bromide 

Downstream Products

• 111061-09-7 (2S,3S)-2-amino-1-phenyl-5-hexen-3-ol 
• 1574312-21-2 (5S,6S)-6-{(tert-butoxycarbonyl)amino}-5-hydroxy-7-phenylhept-2-en-1-yl methyl carbonate 
• 1574312-30-3 (5S,6S)-6-{(tert-butoxycarbonyl)amino}-5-hydroxy-7-phenylhept-2-en-1-yl methyl carbonate 
• 219969-17-2 (4S,5S)-4-Benzyl-5-((S)-2-methanesulfonyloxy-undecyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 219969-15-0 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(2-hydroxyundecyl)-1,3-oxazolidine 
• 219969-14-9 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-formylmethyl-1,3-oxazolidine 
• 210964-94-6 (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine 
• 158527-21-0 tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate 
• 113283-87-7 (4S,5S)-4-benzyl-5-(1-propenyl)-1,3-oxazolidin-2-one 
• 219969-13-8 (4S,5S)-tert-butyl 2,2-dimethyl-4-benzyl-5-prop-2-enyl-1,3-oxazolidine 

Relevant academic research and scientific papers

Stereoselective synthesis of (-)-N-Boc-AHPPA

An efficient method has been developed for the stereoselective synthesis of N-Boc-AHPPA (7), a biologically important amino acid of non-proteinogenic origin.

A practical route to enantiopure 3-hydroxy-pyrrolidines: application to a straightforward synthesis of (-)-bulgecinine

A practical synthesis of enantiopure substituted 3-hydroxy-pyrrolidines is reported. In four steps, starting from commercially available amino acids as chiral educts, this method allows for an efficient preparation of a variety of 3-hydroxy-pyrrolidines, as well as 3-hydroxy-piperidines and azepanes. Application of this methodology for a straightforward asymmetric synthesis of (-)-bulgecinine is also described.

Allyltrichlorostannane additions to α-amino aldehydes: Application to the total synthesis of the aspartyl protease inhibitors L-682,679, L-684,414, L-685,434, and L-685,458

The hydroxyethylene dipeptide isosteres L-682,679, L-684,414, L-685,434, and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-amino aldehyde, followed by hydroboration of the corresponding 1,2-

Stereoselective synthesis of the antifungal antibiotic (+)-preussin

A concise total synthesis of enantiopure (+)-preussin (1) from L- phenylalanine (3) is described. The key steps involve i) syn-selective formation of the 1,2-amino alcohol fragment 2, via chelation controlled addition of allylmagnesium bromide to N-Boc-phenylalaninal, and ii) L- selectride mediated stereoselective reduction of the ketone 8 to the alcohol derivative 9 with the required stereochemistry for final cyclization.

Ring-closing metathesis strategy to unsaturated γ- and δ-lactones: Synthesis of hydroxyethylene isostere for protease inhibitors

Ring-closing olefin metathesis of acrylates derived from allylic and homo allylic alcohols in the presence of the Grubbs' catalyst (10-15 mol%) and titanium isopropoxide (0.3-3 equiv) provided ready access to α, β- unsaturated γ and δ-lactones and an important dipeptide isostere intermediate.

CrCl2 mediated addition of allylic halides or phosphates to N-protected α-amino aldehydes. Stereocontrolled synthesis of a new core for C2 symmetric HIV-protease inhibitors

The addition of γ-monosubstituted allylchromium(III) reagents to N-protected α-amino aldehydes proceeds in a stereoconvergent manner in contrast with the case of the unsubstituted reagents, where the stereoselectivity depends on the nature of the group bo

Addition of Allylic Metals to α-Aminoaldehydes. Application to the Synthesis of Statine, Ketomethylene and Hydroxyethylene Dipeptide Isosteres

A general and stereoselective method to statine, ketomethylene and hydroxyethylene dipeptide isosteres is described.The key reaction is the diastereoselective allyl metal addition to α-aminoaldehydes.