88718-12-1

Basic information

• Product Name: L-Alanine, N-[(phenylmethoxy)carbonyl]-, phenylmethyl ester
• CAS NO: 88718-12-1
• Molecular Formula: C18H19NO4
• Molecular Weight: 313.353
• Mol File: 88718-12-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: L-Alanine, N-[(phenylmethoxy)carbonyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-[(phenylmethoxy)carbonyl]-, phenylmethyl ester(88718-12-1)
• EPA Substance Registry System: L-Alanine, N-[(phenylmethoxy)carbonyl]-, phenylmethyl ester(88718-12-1)

Safety Data

• Hazardous Substances Data: 88718-12-1(Hazardous Substances Data)

Upstream product

• 1142-20-7 N-Cbz-Ala 
• 7285-83-8 2,4,6-tris(benzyloxy)-1,3,5-triazine 
• 65926-39-8 (R)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-iodopropanoate 
• 100-51-6 benzyl alcohol 
• 159390-25-7 2-Benzyl-1,3-bis-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-isourea 
• 79-10-7 acrylic acid 

Downstream Products

• 95617-89-3 Z-(S)-Ala-(S)-Phe-NH₂ 
• 18323-56-3 Z-(S)-Ala-(S)-Leu-NH₂ 
• 50444-54-7 benzyl (S)-1-((S)-1-amino-1-oxopropan-2-ylamino)-1-oxopropan-2-ylcarbamate 
• 4976-59-4 CBZ-L-alanylglycinamide 
• 1142-20-7 N-Cbz-Ala 
• 23458-22-2 Z-(S)-Ala-(S)-Pro-OBzl 
• 136206-25-2 17β-(N-benzyloxycarbonyl-L-alanyl)hydrazonoestra-1,3,5(10)-trien-3-ol 
• 136206-17-2 17β-(N-benzyloxycarbonyl-L-alanyl)aminoestra-1,3,5(10)-trien-3-ol 

Relevant articles and documents

O-Benzylation of Carboxylic Acids Using 2,4,6-Tris(benzyloxy)-1,3,5-triazine (TriBOT) under Acidic or Thermal Conditions

Two methods for the synthesis of benzyl esters from carboxylic acids using the O-benzylating reagent 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT) have been developed. The reactions were conducted either in the presence of a catalytic amount of TfOH at room temperature (acidic conditions) or in the absence of TfOH at 180-230 C (thermal conditions). Interestingly, the O-benzylation of hydroxy carboxylic acids under the two conditions afforded different products: The dibenzylated product under acidic conditions and the hydroxy ester under thermal conditions. In addition to these results, other evidence indicated that the former reaction proceeds through an SN1-type mechanism, and the latter by an SN2-type mechanism. Two methods for the O-benzylation of carboxylic acids using TriBOT have been developed under either acidic or thermal conditions. The O-benzylation of hydroxy carboxylic acids afforded the dibenzylated product under acidic conditions and the hydroxy ester under thermal conditions. The former reaction proceeds through an SN1-type mechanism and the latter by an SN2-type mechanism.

A novel 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)-catalyzed esterification of N-protected amino acids with nearly equimolar amounts of alcohols in the presence of Boc2O

A very mild, BBDI-catalyzed esterification using approximately equimolar amounts of N-protected amino acids and alcohols, in junction with Boc2O is described.

Broadening of the substrate tolerance of α-chymotrypsin by using the carbamoylmethyl ester as an acyl donor in kinetically controlled peptide synthesis

In the kinetically controlled approach of peptide synthesis mediated by α-chymotrypsin, the broadening of the protease's substrate tolerance is achieved by switching the acyl donor from the conventional methyl ester to the carbamoylmethyl ester. Thus, as a typical example, the extremely low coupling efficiency obtained by employing the methyl ester of an inherently poor amino acid substrate, Ala, is significantly improved by the use of this particular ester. Its ameliorating effect is observed also in the couplings of other amino acid residues such as Gly and Ser as carboxy components.