53363-91-0

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 42417-65-2 Z-MeVal-OH 

Downstream Products

• 35016-37-6 N-methyl-L-valine methyl ester 
• 3339-44-4 methyl N-methyl-L-valinate hydrochloride 
• 149357-30-2 (S)-benzyl methyl(3-methyl-1-oxobutan-2-yl)carbamate 
• 42417-65-2 Z-MeVal-OH 
• 128892-33-1 -N-methyl-L-valine methyl ester 
• 128892-32-0 -N-methyl-L-valine methyl ester 
• 128892-35-3 Z-D-MeLeu-MeVal-OMe 
• 128892-34-2 Z-MeLeu-MeVal-OMe 
• 128892-28-4 N--L-N-methylvaline methyl ester 
• 790302-14-6 (S)-2-{[(2S,3S)-3-Benzyloxycarbonylamino-2-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-heptanoyl]-methyl-amino}-3-methyl-butyric acid methyl ester 
• 790302-29-3 (S)-2-{[(2R,3R)-3-Benzyloxycarbonylamino-2-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-heptanoyl]-methyl-amino}-3-methyl-butyric acid methyl ester 
• 790302-30-6 (S)-2-[((2S,3S)-3-Benzyloxycarbonylamino-7-hydroxy-2-methyl-heptanoyl)-methyl-amino]-3-methyl-butyric acid methyl ester 

Relevant academic research and scientific papers

Stereocontrolled synthesis of onchidins

(Chemical Equation Presented) The first total synthesis of a molecule possessing the stereochemistry proposed for onchidin is described. The structure synthesized appears to be different from that of the marine natural product.

Coupling N-Methylated Amino Acids Using PyBroP and PyCloP Halogenophosphonium Salts: Mechanism and Fields of Application

PyBroP (1) and PyCloP (2), two halotripyrrolidinophosphonium hexafluorophosphates, are peptidecoupling reagents highly efficient for coupling N-methylated amino esters, in contrast with PyBOP (3), the hydroxybenzotriazolyl analogue.These halogenophosphonium salts 1 and 2 are convenient (one-pot reactions) stable solids soluble in conventional solvents.Use of them gave an excellent peptide yield with essentially no epimerization.Activation with these reagents probably involves the formation of an (acyloxy)phosphonium, as shown in the case of 2,4,6-trimethylbenzoic acid activation.In the case of reagents 1 and 2, oxazolone and/or a symmetrical anhydride were intermediates which were rapidly aminolyzed.In contrast, the benzotriazolyl ester intermediate which was formed with PyBOP (3) was poorly reactive with N-methylated amino esters.PyBroP (1) and PyCloP (2) were less efficient in the coupling of some Boc-amino acids because of N-carboxyanhydride formation; this was particularly the case when Boc-Val-OH or Boc-MeVal-OH was coupled with MeVal-OMe.

Acyl derivatives

Peptide derivatives provided by the present invention are compounds of the general formula STR1 wherein R1 represents a hydrogen atom or the methyl or hydroxymethyl group or a mono-, di- or trihalomethyl mgroup; R2 represents the cha