Oxiranecarboperoxoic acid, 3-phenyl-, 1,1-dimethylethyl ester, (2R,3S)-

Base Information

• Chemical Name: Oxiranecarboperoxoic acid, 3-phenyl-, 1,1-dimethylethyl ester, (2R,3S)-
• CAS No.: 370084-23-4
• Molecular Formula: C13H16O4
• Molecular Weight: 236.268
• Mol file: 370084-23-4.mol

Synonyms:

Chemical Property of Oxiranecarboperoxoic acid, 3-phenyl-, 1,1-dimethylethyl ester, (2R,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Oxiranecarboperoxoic acid, 3-phenyl-, 1,1-dimethylethyl ester, (2R,3S)-

There total 11 articles about Oxiranecarboperoxoic acid, 3-phenyl-, 1,1-dimethylethyl ester, (2R,3S)- 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:

tert.-butylhydroperoxide (75-91-2) + 3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one (109299-93-6) → (E)-tert-butyl 3-phenylprop-2-eneperoxoate (2123-92-4) + tert-butyl (2S,3R)-3-phenylperoxyglycidate (736141-00-7) + tert-butyl (2R,3S)-3-phenylperoxyglycidate (370084-23-4)

Guidance literature:

With La-(S)-BINOL-Ph₃AsO; 4 A molecular sieve; In tetrahydrofuran; toluene; at 20 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2003.06.010

Reference yield:

tert.-butylhydroperoxide (75-91-2) + cinnamoyl imidazole (1138-15-4,2979-51-3,30802-05-2) → (E)-tert-butyl 3-phenylprop-2-eneperoxoate (2123-92-4) + tert-butyl (2S,3R)-3-phenylperoxyglycidate (736141-00-7) + tert-butyl (2R,3S)-3-phenylperoxyglycidate (370084-23-4)

Guidance literature:

With La-(S)-BINOL-Ph₃AsO; 4 A molecular sieve; In tetrahydrofuran; toluene; at 20 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2003.06.010

Reference yield:

tert.-butylhydroperoxide (75-91-2) + cinnamoyl imidazole (1138-15-4,2979-51-3,30802-05-2) → tert-butyl (2S,3R)-3-phenylperoxyglycidate (736141-00-7) + tert-butyl (2R,3S)-3-phenylperoxyglycidate (370084-23-4)

Guidance literature:

With lanthanum(III) isopropoxide; 4 A molecular sieve; triphenylarsineoxide; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; decane; at 20 ℃; for 3.5h;

DOI:10.1021/ja0164879

upstream raw materials:

tert.-butylhydroperoxide

cinnamoyl imidazole

3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one

4-methyl-1-[(2E)-1-oxo-3-phenyl-2-propenyl]-1H-imidazole

Downstream raw materials:

N-Methyl-α-oxo-3-phenylpropanamide

N-methyl-3-phenylpropanamide

trans-methyl 3-phenylglycidate

methyl (2R,3S)-3-phenylglycidate

Refernces

• 1、 Nemoto,Ohshima,Shibasaki. "Catalytic asymmetric synthesis of α,β-epoxy esters, aldehydes, amides, and γ,δ-epoxy β-keto esters: Unique reactivity of α,β-unsaturated carboxylic acid imidazolides [16]". . p. 9474 - 9475. Retrieved 2007/10/03.