108385-64-4

Upstream product

• 100-39-0 benzyl bromide 
• 119153-87-6 (C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅) 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 110-87-2 3,4-dihydro-2H-pyran 
• 109687-75-4 (4R,5S)-3-((R)-2-Benzyl-4-methyl-pent-3-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 126301-19-7 (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl methanesulfonate 
• 109687-77-6 2-methyl-4(R)-(phenylmethyl)-5-<(2-tetrahydropyranyl)oxy>-2-pentene 
• 108385-58-6 2(S)-(phenylmethyl)-3-<(2-tetrahydropyranyl)oxy>-propionaldehyde 
• 109687-76-5 4-methyl-2(R)-(phenylmethyl)-3-penten-1-ol 
• 109687-70-9 tert-butyl (S)-(1-phenyl-3-(phenylthio)propan-2-yl)carbamate 
• 131915-24-7 [(1S,4S)-2-Benzenesulfonyl-1-benzyl-3-hydroxy-5-phenyl-4-(tetrahydro-pyran-2-yloxymethyl)-pentyl]-carbamic acid tert-butyl ester 

Downstream Products

• 108385-61-1 5(S)--6-phenyl-2(R)-(phenylmethyl)-3-trans-hexenoic acid 
• 155099-12-0 (2R,5S)-2-Benzyl-5-[(tert-butoxycarbonyl)amino]-6-phenyl-(E)-3-hexen-1-ol 

Relevant academic research and scientific papers

New Approaches to the Synthesis of trans-Alkene Isosteres of Dipeptides

Two new syntheses of protected dipeptide analogues bearing a trans carbon-carbon double bond in place of the amide linkage are reported.One route is a linear synthesis employing the rearrangement of an allylic selenide to a protected allylic amine.The second route is convergent and uses the Julia olefin synthesis in a key step.The latter route is fully stereocontrolled and has been used to prepare protected trans-alkene isosteres of the dipeptides TyrAla, PhePhe, LeuPhe, and LeuLeu.

A STEREOCONTROLLED SYNTHESIS OF TRANS-ALKENE ISOSTERES OF DIPEPTIDES

A general synthetic route to trans-alkene isosteres of protected dipeptides is reported.This sequence permits the fully stereocontrolled preparation of these isosteres in optically active form and in quantities sufficient for further biological study.Prep