21691-50-9

Basic information

• Product Name: tert-butyl L-alaninate
• Synonyms: L-Alanine 1,1-dimethylethyl ester;L-Alanine tert-butyl;L-Alanine tert-butyl ester;L-Alanine-tert-butyl ester;Einecs 244-532-3;L-Ala-OBut;-tert-Butyl 2-aminopropanoate;tert-butyl L-alaninate
• CAS NO: 21691-50-9
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.1995
• EINECS: 244-532-3
• Mol File: 21691-50-9.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 163.1°Cat760mmHg
• Flash Point: 37°C
• Appearance: /
• Density: 0.957g/cm³
• Vapor Pressure: 2.1mmHg at 25°C
• Refractive Index: 1.436
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 7.82±0.29(Predicted)
• CAS DataBase Reference: tert-butyl L-alaninate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl L-alaninate(21691-50-9)
• EPA Substance Registry System: tert-butyl L-alaninate(21691-50-9)

Safety Data

• Hazardous Substances Data: 21691-50-9(Hazardous Substances Data)

Usage

General Description

Tert-butyl L-alaninate, also known as tert-butyl Alanine or L-Alanine tert-butyl ester hydrochloride, is a chemical compound used primarily in the field of organic synthesis. Created through esterification of L-Alanine with tert-butanol, it has the molecular formula of C9H19NO2. This chemical compound is an important reagent in chemistry that is also an intermediate for preparing biologically active molecules such as proteins and pharmaceuticals. It is also an ideal building block in peptide synthesis, specifically in organic chemistry for the creation of alanine residues.

InChI:InChI=1/C7H15NO2/c1-5(8)6(9)10-7(2,3)4/h5H,8H2,1-4H3/t5-/m0/s1

Upstream product

• 56-41-7 L-alanin 
• 115-11-7 isobutene 
• 1142-20-7 N-Cbz-Ala 
• 50300-96-4 (S)-2-(benzyloxycarbonylamino)propionic acid tert-butyl ester 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 74-88-4 methyl iodide 
• 875433-32-2 (2S)-N-(9-(4-morpholinophenyl)-9-fluorenyl)alanine tert-butyl ester 
• 875433-31-1 (2S)-N-[9-(4-bromophenyl)-9-fluorenyl]alanine tert-butyl ester 
• 13404-22-3 tert-butyl L-alaninate hydrochloride 
• 540-88-5 acetic acid tert-butyl ester 
• 1245735-66-3 Fms-Ala-OtBu 
• 226900-13-6 tert-butyl N-(diphenylmethylene)alaninate 
• 76849-54-2 t-butyl pyruvate 

Downstream Products

• 58177-77-8 N-[(1,1-dimethylethoxy)carbonyl]-L-alanine 1,1-dimethylethyl ester 
• 2488-22-4 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)propanamido)propanoate 
• 66378-07-2 CARBOBENZYLOXYSARCOSYL-L-ALANINE 
• 66378-00-5 Z-Sar-Ala-O-tBu 
• 62632-23-9 (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)propanoate 
• 53481-48-4 (S)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoate 
• 883725-92-6 ZAFA-t-Bu ester 
• 116912-17-5 N-(Phenylacetyl)-L-alanyl-L-alanin-tert-butylester 
• 33033-71-5 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)propanoate 
• 96896-87-6 N-<3-(ethoxycarbonyl)-2-benzylidene-1-oxopropyl>-L-alanine tert-butyl ester 
• 124201-84-9 (2S)-2-Methyl-6-nitro-3-azaheptandisaeure-1-tert-butyl-7-<2,6-di(tert-butyl)-4-methoxyphenyl>ester 
• 122593-28-6 N²-(tert-butoxycarbonyl)-N³-(benzyloxycarbonyl)-L-(2,3-diaminopropanoyl)-L-alanine tert-butyl ester 
• 116912-19-7 N-(Phenylacetyl)-L-threonyl-L-alanin-tert-butylester 
• 130275-81-9 N-<1(R)-(benzyloxycarbonyl)-3-phenylpropyl>-L-alanine tert-butyl ester 

Relevant articles and documents

Efficient and Divergent Total Synthesis of (-)-Epicoccin G and (-)-Rostratin A Enabled by Double C(sp3)-H Activation

Dithiodiketopiperazines are complex polycyclic natural products possessing a variety of interesting biological activities. Despite their interest, relatively few total syntheses have been completed. We herein report the enantioselective, scalable, and divergent total synthesis of two symmetrical pentacyclic dithiodiketopiperazines, (-)-epicoccin G and (-)-rostratin A. A common intermediate was synthesized on a multigram scale from inexpensive, commercially available starting materials using an enantioselective organocatalytic epoxidation and a double C(sp3)-H activation as key steps, with the latter allowing the efficient simultaneous construction of the two five-membered rings. In addition to the cis,cis-fused target (-)-epiccocin G, the more challenging (-)-rostratin A, possessing two trans ring junctions, was obtained for the first time on a 500 mg scale through the optimization of each step and validation on multigram quantities. Both natural products were synthesized with high overall yields (13-20%). This study should facilitate access to this fascinating and yet understudied family of biologically active natural products.

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

Synthesis of Dipeptides by Boronic Acid Catalysis

We have found that a boronic acid catalyzed amidation of an N -hydroxy amino acid methyl ester with amino acid tert -butyl esters gave N -hydroxy dipeptide derivatives in good yields without any racemization. The protecting groups on the nitrogen atom could be easily removed by heterogeneous hydrogenation conditions.