132682-04-3

Basic information

• Product Name: methyl (S)-2-(2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-2-methylpropanoate
• Synonyms: methyl (S)-2-(2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-2-methylpropanoate
• CAS NO: 132682-04-3
• Molecular Weight: 350.415
• Mol File: 132682-04-3.mol

Chemical Properties

• CAS DataBase Reference: methyl (S)-2-(2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-2-methylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (S)-2-(2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-2-methylpropanoate(132682-04-3)
• EPA Substance Registry System: methyl (S)-2-(2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-2-methylpropanoate(132682-04-3)

Safety Data

• Hazardous Substances Data: 132682-04-3(Hazardous Substances Data)

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 15028-41-8 methyl 2-aminoisobutyrate hydrochloride 
• 13257-67-5 2-amino-2-methylpropionic acid methyl ester 
• 133010-20-5 Cbz-Val-F 

Downstream Products

• 66449-58-9 Z-Val-Aib 
• 150372-62-6 [2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-2-methyl-propionylamino]-acetic acid methyl ester 

Relevant articles and documents

Microwave-enhanced solution coupling of the α,α-dialkyl amino acid, Aib

The difficult coupling of α-aminoisobutyric acid (Aib), during the synthesis of dipeptides (1-6), was carried out using PyBOP/HOBt and HBTU/HOBt reagents by application of microwave energy in the presence of solvent. Room temperature, conventional heating

Efficient coupling of α,α-dimethyl amino acid using a new chloro imidazolidium reagent, CIP

CIP (2-chloro-1,3-dimethylimidazolidium hexafluorophosphate) was an efficient coupling agent for N(α)-protected α-aminoisobutyric acid (Aib) in the presence of an additive. The reactivity was enhanced markedly by a catalytic amount of additive in the order of HOAt ~ HODhbt > DMAP > HOBt. These couplings occurred without detectable racemization.

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

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.

2-Mercaptopyridine-1-oxide-based peptide coupling reagents

The thiouronium salts S-(1-oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) and tetrafluoroborate (TOTT), and S-(1-oxido-2-pyridinyl)-1,3-dimethyl-1,3-trimethylenethiouronium hexafluorophosphate (HODT) and tetrafluoroborate (TODT), prepared from 2-mercaptopyridine-1-oxide and 1,1,3,3-tetramethylurea (TMU) or 1,3-dimethylpropyleneurea (DMPU), have been employed as reagents in solution and solid-phase peptide coupling chemistry. Furthermore, 2-mercaptopyridine-1-oxide has been employed as racemization-reducing additive combined with the new thiouronium salts and other frequently used peptide coupling reagents such as DCC or TBTU.

Convergent synthesis of (-)-mirabazole C using a chloroimidazolidium coupling reagent, CIP

Convergent synthesis of (-)-mirabazole C (1), a tetra thiazoline/thiazole alkaloid isolated from blue-green alga, has been described. The successive thiazoline rings of (-)-mirabazole C were formed by a single-step cyclization mediated by TiCl4 treatment of tripeptide amide 4. Convergent synthesis of the key intermediate 33 derived from three 2-methylcysteine residues was first achieved using a newly developed coupling reagent, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP). The effectiveness of CIP for the coupling of α,α-dialkyl amino acids and the reaction pathway of the activation were clarified by the syntheses of model peptides containing an α,α-dimethylamino acid. A practical method of asymmetric synthesis of 2-methylcysteine by alkylation of 2,4-cis-oxazolidinone 23 has also been described.

Efficient synthesis of alamethicin F-30 using a chloro imidazolidium coupling reagent, CIP

Alamethicin F-30 has been synthesized in solution using a CIP-additive as a coupling agent and TFA as a final deprotecting reagent. All couplings including those between sterically hindered α,α-dimethyl amino acid were successfully achieved by a 60 min re

PyBOP and PyBroP: Two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib

The difficult coupling of α-aminoisobutyric acid (Aib) was carried out using PyBOP and PyBroP in a comparative study with BOP and BroP. These reagents gave good results under simple conditions (one pot, r.t., 1h). Coded amino acids could be coupled with Aib using PyBOP under standard conditions of peptide synthesis without racemization whereas the coupling of two Aib residues required PyBroP/DMAP. A fragment containing an Aib C-terminal could be coupled without epimerization of the penultimate residue.