869772-05-4

Basic information

• Product Name: benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate
• Synonyms: benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate
• CAS NO: 869772-05-4
• Molecular Weight: 384.459
• Mol File: 869772-05-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate(869772-05-4)
• EPA Substance Registry System: benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate(869772-05-4)

Safety Data

• Hazardous Substances Data: 869772-05-4(Hazardous Substances Data)

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 1152-62-1 Cbz-Met-OH 

Downstream Products

• 886981-35-7 2((S)-2-benzyloxycarbonylamino-4-methylsulfanylbutyrylamino)propanoic acid 
• 113756-87-9 methyl 2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-(methylsulfanyl)butanoyl]amino}-2-methylpropanoate 
• 1450900-23-8 C₂₀H₂₆N₄O₅S 
• 1574526-69-4 (Z)-L-Met-Tau-OH 
• 1309439-90-4 C₂₃H₃₅NO₆S 
• 1309439-89-1 C₂₂H₂₅NO₆S 
• 1309440-05-8 C₂₈H₃₆N₂O₇S 
• 1309440-06-9 C₂₁H₃₀N₂O₇S 
• 1260405-39-7 N-Z-L-Met-L-Cys-OH 
• 1260405-49-9 Z-L-Met-L-Cys(Z-L-Met)-OH 
• 1194481-51-0 Cbz-L-Met-L-AOAla-OH 
• 1194481-49-6 Cbz-L-Met-AOGly-OH 
• 1052265-65-2 (S)-2-((S)-2-benzyloxycarbonylamino-4-methylsulfanylbutanoylamino)-5-guanidinopentanoic acid 
• 1039553-02-0 benzyl N-{(1S)-3-methylsulfanyl-1-[(2-pyridinylamino)carbonyl]propyl}carbamate 

Relevant articles and documents

Non-phosgene route to unsymmetrical ureas from N-Cbz-α-amino acid amides

A convenient method toward the synthesis of α-amino acid-derived unsymmetrical ureas 2 is described herein. This route involves an interesting rearrangement of amides of N-Cbz-α-amino acids 1, which presumably entails the intermediacy of hydantoins that is followed by hydrolysis to afford unsymmetrical ureas 2 in quantitative yields and high purity.

Benzotriazole-mediated syntheses of depsipeptides and oligoesters

Reactions of O-Pg(α-hydroxyacyl)benzotriazoles with (a) unprotected α-hydroxycarboxylic acids, (b) amino acids, and (c) amines afforded, respectively, chirally pure (a) oligoesters, (b) depsidipeptides, and (c) amide conjugates (yields 52-94%). N-Pg(α-Ami

The efficient preparation of di- and tripeptides by coupling N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles with unprotected amino acids

N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles 2 and N-protected peptidoylbenzotriazoles 6 are coupled in aqueous acetonitrile solution with free amino acids or dipeptides to prepare: (i) 22 chirally pure dipeptides 5a-v (in an average yield of 82%) from N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles 2 and unprotected amino acids, (ii) five chiral tripeptides 7a-e (in an average yield of 75%) from N-protected peptidoylbenzotriazoles 6 and unprotected amino acids, (iii) one chiral tripeptide 7g (62%) from N-(Cbz- or Fmoc-α- aminoacyl)benzotriazole 2a and the free dipeptide 8. In all, N-(Cbz- or Fmoc-α-aminoacyl)benzotriazole derivatives of 17 of the 20 naturally occurring amino acids were used, including those containing the following unprotected side chain functionalities: alcoholic -OH (Ser), indole -NH (Trp), imidazole -NH, phenolic -OH (Tyr), -CONH2 (Gln, Asn), -SH (Cys), -CO2H (Glu, Asp), and -S-S (Cystine). Support for the complete retention of chirality was obtained by parallel experiments involving D-Ala, L-Ala, and DL-Ala for the preparation of di- and tripeptides. This and other evidence for chiral integrity was supported by NMR and HPLC analyses. Georg Thieme Verlag Stuttgart.