(S)-3-Methyl-4-(benzyloxy)butyric acid

Base Information

• Chemical Name: (S)-3-Methyl-4-(benzyloxy)butyric acid
• CAS No.: 64190-49-4
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• DSSTox Substance ID: DTXSID80428309
• Nikkaji Number: J416.304D
• Wikidata: Q82241132
• Mol file: 64190-49-4.mol

Synonyms:AC1OGROT;64190-49-4;SCHEMBL4433522;DTXSID80428309;(S)-3-Methyl-4-(benzyloxy)butyric acid

Chemical Property of (S)-3-Methyl-4-(benzyloxy)butyric acid

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 185

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)O)COCC1=CC=CC=C1
• Isomeric SMILES: C[C@@H](CC(=O)O)COCC1=CC=CC=C1

Technology Process of (S)-3-Methyl-4-(benzyloxy)butyric acid

There total 17 articles about (S)-3-Methyl-4-(benzyloxy)butyric 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: 94.0%

(3S)-4-Benzyloxy-3-methyl-butyraldehyde (90865-69-3) → (S)-4-(Benzyloxy)-3-methylbutanoic acid (64190-49-4)

Guidance literature:

With silver(l) oxide;

DOI:10.1002/hlca.19900730516

Reference yield: 84.0%

methylmagnesium bromide (75-16-1) + 4-(R)-benzyloxymethyl-β-propiolactone (252873-91-9) → (S)-4-(Benzyloxy)-3-methylbutanoic acid (64190-49-4)

Guidance literature:

methylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; dimethylsulfide; In diethyl ether; at -50 - -30 ℃;

4-(R)-benzyloxymethyl-β-propiolactone; In diethyl ether; at -50 ℃; for 0.5h;

With chloro-trimethyl-silane; In diethyl ether; at -50 - 20 ℃; Further stages.;

DOI:10.1021/jo025519n

Reference yield:

(E)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-2-enylamine (90809-13-5) → (S)-4-(Benzyloxy)-3-methylbutanoic acid (64190-49-4)

Guidance literature:

Multi-step reaction with 3 steps

1: ClO₄ / tetrahydrofuran / 137 h / 65 °C

2: aq. AcOH

3: 94 percent / Ag₂O

With acetic acid; silver(l) oxide; ClO4; In tetrahydrofuran;

DOI:10.1002/hlca.19900730516

upstream raw materials:

(3S)-4-Benzyloxy-3-methyl-butyraldehyde

methylmagnesium bromide

4-(R)-benzyloxymethyl-β-propiolactone

(2S)-1-(benzyloxy)propan-2-ol

Downstream raw materials:

(1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate

C₂₂H₂₅NO₄

C₂₂H₂₄N₄O₄

C₁₃H₁₈N₄O₂

Refernces

• 1、 Pronin, Sergey V.,Kozmin, Sergey A.. "Synthesis of streptolydigin, a potent bacterial RNA polymerase inhibitor". supporting information; experimental part. p. 14394 - 14396. Retrieved 2010/12/24.
• 2、 Berens,Scharf. "A new synthesis of (S)-β-methyl-γ-butyrolactone and (S)-4-benzyloxy-3-methylbutanoic acid". . p. 832 - 834. Retrieved 2007/10/02.