D-Isovaline

Base Information

• Chemical Name: D-Isovaline
• CAS No.: 3059-97-0
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• Hs Code.: 29224985
• UNII: IF7U5GXQ28
• DSSTox Substance ID: DTXSID501016649
• Nikkaji Number: J9.209F
• Wikidata: Q27095005
• Metabolomics Workbench ID: 148642
• Mol file: 3059-97-0.mol

Synonyms:14C-AMB;2-amino-2-methylbutanoic acid;2-ethylalanine;alpha-amino-2-methylbutanoic acid;alpha-ethylalanine;isovaline;isovaline hydrochloride, (D)-isomer;isovaline hydrochloride, (DL)-isomer;isovaline, (D)-isomer;isovaline, (DL)-isomer;isovaline, monosodium salt;isovaline, monosodium salt, (D)-isomer

Chemical Property of D-Isovaline

Chemical Property:

• Appearance/Colour: White needles or crystalline powder
• Vapor Pressure: 0.0633mmHg at 25°C
• Melting Point: 276-278 °C (lit.)
• Refractive Index: 1.465
• Boiling Point: 213.6 °C at 760 mmHg
• PKA: 2.38±0.10(Predicted)
• Flash Point: 83 °C
• PSA: 63.32000
• Density: 1.07 g/cm³
• LogP: 0.89870
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: freely soluble
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

D-Isovaline 97% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of D-Isovaline

There total 47 articles about D-Isovaline 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: 100.0%

benzyl (R)-2-azido-2-methylbutanoate (1092559-79-9) → (2R)-2-amino-2-methylbutanoic acid (3059-97-0,465-58-7)

Guidance literature:

With 1% Pd/C; hydrogen; In methanol; at 20 ℃;

DOI:10.3987/REV-09-SR(S)1

Reference yield: 89.0%

(R)-2-Amino-2-methyl-butyric acid ethyl ester (40916-97-0) → (2R)-2-amino-2-methylbutanoic acid (3059-97-0,465-58-7)

Guidance literature:

With water; sodium hydroxide; In ethanol; for 4h; Reflux;

Reference yield: 76.0%

(R)-2-amino-2-methylbutanoic acid tert-butyl ester → (2R)-2-amino-2-methylbutanoic acid (3059-97-0,465-58-7)

Guidance literature:

(R)-2-amino-2-methylbutanoic acid tert-butyl ester; With methanesulfonic acid; In 1,2-dichloro-ethane; at 25 - 80 ℃; for 13h;

With triethylamine; In 1,2-dichloro-ethane; at 25 ℃; for 16h;

upstream raw materials:

N-chloroacetyl-D-isovaline

DL-isovaline

4-ethyl-4-methyl-2-phenyl-4H-oxazol-5-one

ethyl bromide

Downstream raw materials:

(2R)-2-amino-2-methylbutanoic acid hydrochloride

(5R)-5-ethyl-5-methylimidazolidine-2,4-dione

Refernces

• 1、 Lee, Jin Woo,Collins, Jennifer E.,Wendt, Karen L.,Chakrabarti, Debopam,Cichewicz, Robert H.. "Leveraging Peptaibol Biosynthetic Promiscuity for Next-Generation Antiplasmodial Therapeutics". supporting information. p. 503 - 517. Retrieved 2021/03/01.
• 2、 Nojiri, Masutoshi,Yoshida, Fumi,Hirai, Yoshinori,Nishiyama, Akira,Yasohara, Yoshihiko. "A practical chemoenzymatic synthesis of (R)-isovaline based on the asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide". . p. 1 - 5. Retrieved 2015/03/31.