(2R,3S)-2-acetamido-3-methylpentanoic acid

Base Information

• Chemical Name: (2R,3S)-2-acetamido-3-methylpentanoic acid
• CAS No.: 54831-20-8
• Molecular Formula: C8H15NO3
• Molecular Weight: 173.212
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID80879251
• Nikkaji Number: J102.444B
• Wikidata: Q82861319
• Mol file: 54831-20-8.mol

Synonyms:N-Acetyl-D-allo-isoleucine;54831-20-8;Acetyl-d-alloisoleucine;(2R,3S)-2-acetamido-3-methylpentanoic acid;D-Alloisoleucine, N-acetyl-;N-Acetyl-D-alloisoleucine;Acetyl-D-allo-isoleucine;MFCD00136538;19764-31-9;SCHEMBL7775372;DTXSID80879251;CHEBI:167745;AKOS006274146;AS-31834;CS-0153941;N-Acetyl-D-allo-isoleucine (Ac-D-aIle-OH);EN300-7395748;A870344

Chemical Property of (2R,3S)-2-acetamido-3-methylpentanoic acid

Chemical Property:

• Melting Point: 154-155.5 °C
• Boiling Point: 369.7±25.0 °C(Predicted)
• PKA: 3.67±0.10(Predicted)
• PSA: 66.40000
• Density: 1.069±0.06 g/cm3(Predicted)
• LogP: 1.01270
• Storage Temp.: -20°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Ethanol (Slightly), Methanol (Sl
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 173.10519334
• Heavy Atom Count: 12
• Complexity: 179

Purity/Quality:

98%Min ^*data from raw suppliers

N-Acetyl-D-allo-isoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)NC(=O)C
• Isomeric SMILES: CC[C@H](C)[C@H](C(=O)O)NC(=O)C

Technology Process of (2R,3S)-2-acetamido-3-methylpentanoic acid

There total 50 articles about (2R,3S)-2-acetamido-3-methylpentanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + acetic anhydride (108-24-7) → (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid (5854-47-7,19764-31-9,20257-17-4,33601-90-0,54831-20-8,73465-39-1,3077-46-1)

Guidance literature:

In methanol; Reflux;

DOI:10.1002/anie.201611852

Reference yield: 87.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + acetyl chloride (75-36-5) → (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid (5854-47-7,19764-31-9,20257-17-4,33601-90-0,54831-20-8,73465-39-1,3077-46-1)

Guidance literature:

In water; at 110 ℃; for 0.0833333h; chemoselective reaction; Microwave irradiation; Green chemistry;

DOI:10.1039/c4ra16683c

Reference yield: 72.0%

N-Ac-Ile-OMe → (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid (5854-47-7,19764-31-9,20257-17-4,33601-90-0,54831-20-8,73465-39-1,3077-46-1)

Guidance literature:

With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4; In tetrahydrofuran; Ambient temperature;

upstream raw materials:

L-isoleucine

acetic anhydride

acetic acid

D-alloisoleucine

Downstream raw materials:

Ac-ISVU(Ph)RSTS

N-acetyl-L-isoleucyl-O-benzyl-L-tyrosine methyl ester

D-allo-isoleucine

L-isoleucine

Refernces

• 1、 Chen, Lei,Du, Ding,Feng, Jie,Gao, Jian,Lu, Tao,Ma, Rui,Shi, Zhihao,Zhang, Kuili. "Bio- And Medicinally Compatible α-Amino-Acid Modification via Merging Photoredox and N-Heterocyclic Carbene Catalysis". supporting information. . Retrieved 2020/09/02.
• 2、 -. "GRANZYME B DIRECTED IMAGING AND THERAPY". Page/Page column 108; 109; 146. . Retrieved 2019/09/04.