t-butyl cis-β-phenylglycidate

Base Information

• Chemical Name: t-butyl cis-β-phenylglycidate
• CAS No.: 201804-25-3
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.268
• Mol file: 201804-25-3.mol

Synonyms:t-butyl cis-β-phenylglycidate

Chemical Property of t-butyl cis-β-phenylglycidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of t-butyl cis-β-phenylglycidate

There total 4 articles about t-butyl cis-β-phenylglycidate 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: 99.0%

(Z)-tert-butyl 3-phenylprop-2-enoate (7042-36-6,14990-09-1,68872-73-1) → t-butyl cis-β-phenylglycidate (201804-25-3)

Guidance literature:

With 2-Ethylhexanoic acid; (S,S)-Mn-dpn; dihydrogen peroxide; at -35.16 ℃; for 3.5h; enantioselective reaction;

DOI:10.1002/tcr.201700032

Reference yield: 80.0%

(2S,3S)-3-Chloro-2-hydroxy-3-phenyl-propionic acid tert-butyl ester → t-butyl cis-β-phenylglycidate (201804-25-3)

Guidance literature:

With Amberlite IRA 420; In tetrahydrofuran; Ambient temperature;

Reference yield:

tert-butyl 3-phenyloxirane-2-carboxylate (27593-40-4) → t-butyl cis-β-phenylglycidate (201804-25-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / HCl / CH₂Cl₂ / 0.5 h / 0 °C

2: 80 percent / Amberlite IRA 420 (OH) / tetrahydrofuran / Ambient temperature

With hydrogenchloride; Amberlite IRA 420; In tetrahydrofuran; dichloromethane;

upstream raw materials:

tert-butyl 3-phenyloxirane-2-carboxylate

(Z)-tert-butyl 3-phenylprop-2-enoate

Downstream raw materials:

(2R,3S)-tert-butyl 3-benzamido-2-hydroxy-3-phenylpropanoate

(2R,3S)-N-benzoyl-3-phenylisoserine

(2R,3S)-tert-butyl 3-azido-2-hydroxy-3-phenylpropanoate

(2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid tert-butyl ester

Refernces

• 1、 Adger, Brian M.,Barkley, James V.,Bergeron, Sophie,Cappi, Michael W.,Flowerdew, Benjamin E.,Jackson, Mark P.,McCague, Ray,Nugent, Thomas C.,Roberts, Stanley M.. "Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones: Total synthesis of diltiazem and Taxol side-chain". . p. 3501 - 3507. Retrieved 2007/10/03.