Benzyl (S)-oxirane-2-carboxylate

Base Information

• Chemical Name: Benzyl (S)-oxirane-2-carboxylate
• CAS No.: 110994-90-6
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.188
• European Community (EC) Number: 631-257-2
• Mol file: 110994-90-6.mol

Synonyms:110994-90-6;Benzyl (S)-oxirane-2-carboxylate;benzyl (2S)-oxirane-2-carboxylate;EN300-8173460;Z1278925196

Chemical Property of Benzyl (S)-oxirane-2-carboxylate

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 185

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(O1)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1[C@H](O1)C(=O)OCC2=CC=CC=C2

Technology Process of Benzyl (S)-oxirane-2-carboxylate

There total 1 articles about Benzyl (S)-oxirane-2-carboxylate 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: 65.0%

benzyl bromide (100-39-0) + potassium de l'acide (S)-(-)-epoxy-2,3 propionique (82079-45-6) → (S)-(-)-glycidate de benzyle (110994-90-6)

Guidance literature:

With 18-crown-6 ether; In acetonitrile;

DOI:10.1016/S0040-4039(00)96028-3

Reference yield:

(S)-(-)-glycidate de benzyle (110994-90-6) → benzyl(2S)-2-methoxy-4-pentynoate (179943-75-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi, 2.) EtAlCl

2: 72 percent / Ag₂O / CH₂Cl₂ / 24 h / 50 °C

3: 81 percent / aq. KF / dimethylformamide / 20 h

With potassium fluoride; n-butyllithium; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9607796

Reference yield:

(S)-(-)-glycidate de benzyle (110994-90-6) → (S)-2-Methoxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester (179943-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi, 2.) EtAlCl

2: 72 percent / Ag₂O / CH₂Cl₂ / 24 h / 50 °C

With n-butyllithium; silver(l) oxide; In dichloromethane;

DOI:10.1021/ja9607796

upstream raw materials:

benzyl bromide

potassium de l'acide (S)-(-)-epoxy-2,3 propionique

Downstream raw materials:

(S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester

benzyl(2S)-2-methoxy-4-pentynoate

(S)-2-Methoxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester