benzyl(S)-valinol

Base Information

• Chemical Name: benzyl(S)-valinol
• CAS No.: 42807-42-1
• Molecular Formula: C12H19NO
• Molecular Weight: 193.289
• DSSTox Substance ID: DTXSID80436429
• Nikkaji Number: J1.045.757B
• Wikidata: Q82251697
• Mol file: 42807-42-1.mol

Synonyms:benzyl(S)-valinol;42807-42-1;N-Benzyl-L-valinol;benzyl (S)-valinol;N-benzyl (s)-valinol;SCHEMBL11972180;DTXSID80436429;HQUYDMGPGDLNJM-GFCCVEGCSA-N;AKOS017531242;(S)-2-(benzylamino)-3-methylbutan-1-ol

Chemical Property of benzyl(S)-valinol

Chemical Property:

• PSA: 32.26000
• LogP: 2.18400
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 193.146664230
• Heavy Atom Count: 14
• Complexity: 141

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CO)NCC1=CC=CC=C1
• Isomeric SMILES: CC(C)[C@@H](CO)NCC1=CC=CC=C1

Technology Process of benzyl(S)-valinol

There total 27 articles about benzyl(S)-valinol 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: 98.0%

(S)-valinol (2026-48-4,473-75-6) + benzaldehyde (100-52-7) → N-benzyl-L-valinol (42807-42-1)

Guidance literature:

(S)-valinol; benzaldehyde; In methanol; at 20 ℃; for 24h;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1021/jo016068u

Reference yield: 97.0%

L-valine benzyl ester p-toluenesulfonate salt (16652-76-9) + benzoic acid anhydride (93-97-0) → N-benzyl-L-valinol (42807-42-1)

Guidance literature:

L-valine benzyl ester p-toluenesulfonate salt; benzoic acid anhydride; With triethylamine; In dichloromethane; for 1h; Inert atmosphere;

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2.25h; Inert atmosphere; Reflux;

DOI:10.1021/acs.joc.1c00378

Reference yield: 96.0%

N-benzylidene-L-valinol (84983-97-1) + allyl bromide (106-95-6) → N-benzyl-L-valinol (42807-42-1) + (2S)-3-methyl-2-((1S)-1-phenylbut-3-enylamino)butan-1-ol (154228-41-8) + (2S)-3-methyl-2-((1R)-1-phenylbut-3-enylamino)butan-1-ol

Guidance literature:

N-benzylidene-L-valinol; samarium; trimethylaluminum; In hexane; at 0 ℃;

allyl bromide; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo0014616

upstream raw materials:

N-benzoyl-L-valine

ethyl (S)-N-benzylvalinate

(S)-valinol

benzaldehyde

Downstream raw materials:

(2R,4S)-2-vinyl-1,3,2-oxapospholidin-2-one

(1'S,2S,4S)-3-benzyl-2-<1'-(dibenzylamino)ethyl>-4-(methylethyl)-1,3-oxazolidine

(S)-valinol

3-benzyl-(4S)-isopropyl-1,3-oxazolidin-2-one

Refernces

• 1、 Zhang, Junhui,Dai, Lixiong,Webster, Alexandra M.,Chan, Wesley Ting Kwok,Mackenzie, Lewis E.,Pal, Robert,Cobb, Steven L.,Law, Ga-Lai. "Unusual Magnetic Field Responsive Circularly Polarized Luminescence Probes with Highly Emissive Chiral Europium(III) Complexes". supporting information. p. 1004 - 1010. Retrieved 2020/11/30.
• 2、 Chen, Ning,Li, Xiang,Xu, Jiaxi. "Microwave-Assisted CuCl-Catalyzed Three-Component Reactions of Alkynes, Aldehydes, and Amino Alcohols". supporting information. p. 3336 - 3344. Retrieved 2019/08/28.