4474-95-7

Basic information

• Product Name: L-Isoleucine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester
• Synonyms: N-benzyloxycarbonyl-L-phenylalanyl-L-isoleucine methyl ester;Z-L-Phe-L-Ile-OMe;Z-Phe-Ile-OMe;(2S,3S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-methyl-pentanoic acid methyl ester;N-Benzyloxycarbonyl-L-phenylalanyl-L-isoleucin-methylester;Cbz-L-Phe-L-Ile-OMe;Z-L-Phe-L-lle-OMe
• CAS NO: 4474-95-7
• Molecular Formula: C24H30N2O5
• Molecular Weight: 426.513
• Mol File: 4474-95-7.mol

Chemical Properties

• Melting Point: 105 - 107 °C
• CAS DataBase Reference: L-Isoleucine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Isoleucine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(4474-95-7)
• EPA Substance Registry System: L-Isoleucine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(4474-95-7)

Safety Data

• Hazardous Substances Data: 4474-95-7(Hazardous Substances Data)

Upstream product

• 1161-13-3 N-Cbz-L-Phe 
• 18598-74-8 methyl L-isoleucinate hydrochloride 
• 128254-45-5 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 2,4-bis-methanesulfonyl-naphthalen-1-yl ester 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 2577-46-0 L-isoleucine methyl ester 
• 18598-74-8 (S)-methyl 2-amino-3-methylpentanoate hydrochloride 
• 54769-22-1 1-methanesulfonyloxy-1,2,3-benzotriazole 

Downstream Products

• 47166-12-1 H-Phe-Ile-OMe 

Relevant articles and documents

Phosphorus pentoxide for amide and peptide bond formation with minimal by-products

Phosphorus pentoxide and DMAP are used for amide bond formation from carboxylic acids and amines. Dipeptides and amides have been synthesized using this reagent in 42–77% yields and >99% ees. The protocol is attractive as it occurs at ambient temperature, the formation of organic by-products is minimal and the reagent can be readily quenched using water. Furthermore, excellent enantioselectivities are observed without the use of harsh triazole based additives.

Practical Peptide Synthesis Mediated by a Recyclable Hypervalent Iodine Reagent and Tris(4-methoxyphenyl)phosphine

6-(3,5-Bis(trifluoromethyl)phenyl)-1H,4H-2aλ3-ioda-2,3-dioxacyclopenta[hi]indene-1,4-dione (p-BTFP-iodosodilactone, 1a) was synthesized and demonstrated to be an efficient hypervalent iodine(III) reagent for the synthesis of dipeptides from various standard amino acids, including sterically hindered amino acids, in good to high yields within 30 min in the presence of tris(4-methoxyphenyl)phosphine. In addition, the combined system of 1a/(4-MeOC6H4)3P was used to synthesize the pentapeptide leu-enkephalin in protected form. It is worth noting that 1a can be regenerated readily after reaction.

Recyclable hypervalent iodine(III) reagent iodosodilactone as an efficient coupling reagent for direct esterification, amidation, and peptide coupling

A hypervalent iodine(III) reagent plays a novel role as an efficient coupling reagent to promote the direct condensation between carboxylic acids and alcohols or amines to provide esters, macrocyclic lactones, amides, as well as peptides without racemization. The regeneration of iodosodilactone (1) can also be readily achieved. The intermediate acyloxyphosphonium ion C from the activation of a carboxylic acid is thought to be involved in the present esterification reaction.

PREPARATION OF 2,4-BIS(METHYLSULFONYL)-1-NAPHTHYL ("BMSN") ACTIVE ESTERS AND THEIR POTENTIAL UTILITY IN PEPTIDE BOND FORMATION

A convenient synthesis of 2,4-bis(methylthio)-1-naphthol and 2,4-bis(methylsulfonyl)-1-naphthol is reported.The utility of the latter as a carboxyl-activating component in the formation of peptide bonds is also presented.

Sulfonic acid esters

A novel process for the amidation or esterification which comprises reacting a compound having a carboxy group with a compound having an amino or imino group which can be acylated or with a compound having a hydroxy group in the presence of a sulfonic acid ester of the formula: wherein R1 is an organic group and R2 O-- is a residue of a strongly acidic N-hydroxy compound as a condensation agent, and a novel sulfonic acid ester useful as such a condensation agent and a process for the preparation thereof.