(S)-tert-Butyl 2-hydroxy-3-phenylpropanoate

Base Information

• Chemical Name: (S)-tert-Butyl 2-hydroxy-3-phenylpropanoate
• CAS No.: 7622-23-3
• Molecular Formula: C13H18 O3
• Molecular Weight: 222.284
• DSSTox Substance ID: DTXSID801234561
• Nikkaji Number: J74.244I
• Mol file: 7622-23-3.mol

Synonyms:7622-23-3;(S)-tert-Butyl 2-hydroxy-3-phenylpropanoate;tert-butyl (2S)-2-hydroxy-3-phenylpropanoate;Benzenepropanoic acid,a-hydroxy-, 1,1-dimethylethyl ester,(S)-;DTXSID801234561;MFCD11042373;AKOS015911902;AS-71324;CS-0000168;tert-Butyl (S)-2-hydroxy-3-phenylpropanoate;N10569;1,1-Dimethylethyl (alphaS)-alpha-hydroxybenzenepropanoate;Benzenepropanoic acid,-hydroxy-, 1,1-dimethylethyl ester, (S)-

Chemical Property of (S)-tert-Butyl 2-hydroxy-3-phenylpropanoate

Chemical Property:

• Melting Point: 34 °C
• Boiling Point: 320.3±22.0 °C(Predicted)
• PKA: 13.00±0.20(Predicted)
• PSA: 46.53000
• Density: 1.077±0.06 g/cm3(Predicted)
• LogP: 1.93170
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 222.125594432
• Heavy Atom Count: 16
• Complexity: 224

Purity/Quality:

97% ^*data from raw suppliers

(S)-tert-Butyl2-hydroxy-3-phenylpropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CC1=CC=CC=C1)O
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CC1=CC=CC=C1)O
• Uses: (S)-tert-Butyl 2-hydroxy-3-phenylpropanoate is used in the synthetic preparation of clavatustides A (C563723) and B (C563725) and their enantiomers by esterification via ring opening of benzoxazinones

Technology Process of (S)-tert-Butyl 2-hydroxy-3-phenylpropanoate

There total 6 articles about (S)-tert-Butyl 2-hydroxy-3-phenylpropanoate 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: 89.0%

L-tert-butyl 2-acetyloxy-3-phenylpropanoate (7678-28-6) → L-α-hydroxyhydrocinnamic acid t-butyl ester (7622-23-3)

Guidance literature:

With potassium carbonate; In methanol; water; at 20 ℃; for 12h;

DOI:10.1021/jo010376a

Reference yield:

(S)-3-phenyl-2-acetyloxypropionic acid (33173-31-8) → L-α-hydroxyhydrocinnamic acid t-butyl ester (7622-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / DMAP; DCC / CH₂Cl₂ / 12 h / 20 °C

2: 89 percent / K₂CO₃ / methanol; H₂O / 12 h / 20 °C

With dmap; potassium carbonate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water;

DOI:10.1021/jo010376a

Reference yield:

L-3-phenyllactic acid (20312-36-1) + tert-butyl alcohol (75-65-0) → L-α-hydroxyhydrocinnamic acid t-butyl ester (7622-23-3)

Guidance literature:

With copper(l) chloride; diisopropyl-carbodiimide; Yield given. Multistep reaction; 1.) 4 d, 2.) CH₂Cl₂, r.t., 18 h;

DOI:10.1021/jo00120a022

upstream raw materials:

L-tert-butyl 2-acetyloxy-3-phenylpropanoate

L-3-phenyllactic acid

tert-butyl alcohol

L-phenylalanine

Downstream raw materials:

(-)-(2S)-trifluoromethanesulfonyloxy-3-phenyl-propionic acid tert-butyl ester

D-tert-butyl 2-phthalimid-N-oxy-3-phenylpropanoate

t-butyl (RS)-phenylalaninate

D-tert-butyl 2-p-chlorophenylcarbonyl-aminoxy-3-phenylpropanoate