(2R,3S)-2-Methyl-3-hydroxyvaleric acid

Base Information

• Chemical Name: (2R,3S)-2-Methyl-3-hydroxyvaleric acid
• CAS No.: 77302-11-5
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• DSSTox Substance ID: DTXSID80439511
• Nikkaji Number: J1.372.589F
• Wikidata: Q82255471
• Mol file: 77302-11-5.mol

Synonyms:77302-11-5;(2R,3S)-2-Methyl-3-hydroxyvaleric acid;(2R,3S)-3-hydroxy-2-methylpentanoic acid;CTK2G6651;DTXSID80439511;AKOS006371768;EN300-2956230

Chemical Property of (2R,3S)-2-Methyl-3-hydroxyvaleric acid

Chemical Property:

• PSA: 57.53000
• LogP: 0.47800
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2R,3S)-2-Methyl-3-hydroxyvaleric acid

There total 24 articles about (2R,3S)-2-Methyl-3-hydroxyvaleric 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%

(4SR,5SR)-2,5-dihydroxy-2,4-dimethyl-2-O-trimethylsilylheptan-3-one (119460-80-9,122706-12-1) → (2SR,3RS)-3-hydroxy-2-methylpentanoic acid (28892-73-1,77302-11-5,77405-43-7,81873-63-4,93861-71-3,98524-11-9,98524-12-0,109215-41-0,131897-89-7)

Guidance literature:

With periodic acid; In methanol; water; at 25 ℃; for 12h;

Reference yield: 85.0%

[2R,3S,1'S,2'S]-(+)-N-(2'hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-pentanamide (219783-13-8) → [2R,3S]-(-)-3-hydroxy-2-methylpentanoic acid (77302-11-5) + pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; for 2h; Heating;

DOI:10.1021/jo000035h

Reference yield: 39.0%

2',6'-bis(1,1-dimethylethyl)-4'-methoxyphenyl (2SR,3SR)-2-methyl-3-hydroxyopentanoate (81818-94-2) → (2SR,3SR)-2-methyl-3-hydroxypentanoic acid (28892-73-1,77302-11-5,77405-43-7,81873-63-4,93861-71-3,98524-11-9,98524-12-0,109215-41-0,131897-89-7)

Guidance literature:

With ammonium cerium(IV) nitrate; mannitol; In acetonitrile; for 0.5h;

DOI:10.1016/S0040-4020(01)93284-3

upstream raw materials:

[2R,3S,1'S,2'S]-(+)-N-(2'hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-pentanamide

(3R^*,4R^*)-4-hydroxy-3-methylhexene

(4SR,5SR)-2,5-dihydroxy-2,4-dimethyl-2-O-trimethylsilylheptan-3-one

propionaldehyde

Downstream raw materials:

(2S,3S)-2-methylpentane-1,3-diol

(2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol

(2S,3S)-3-O-acetyl-2-methyl-1-O-p-toluenesulfonyl-1,3-pentanediol

Toluene-4-sulfonic acid (2S,3S)-3-methoxymethoxy-2-methyl-pentyl ester