(1RS,2SR)-1-phenylpropane-1,2-diyl diacetate

Base Information

• Chemical Name: (1RS,2SR)-1-phenylpropane-1,2-diyl diacetate
• CAS No.: 21145-69-7
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 21145-69-7.mol

Synonyms:

Chemical Property of (1RS,2SR)-1-phenylpropane-1,2-diyl diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1RS,2SR)-1-phenylpropane-1,2-diyl diacetate

There total 21 articles about (1RS,2SR)-1-phenylpropane-1,2-diyl diacetate 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: 80.0%

cis-1-phenyl-1-propylene (766-90-5) + acetic anhydride (108-24-7) → (1RS,2SR)-1-phenylpropane-1,2-diyl diacetate (21145-69-7,21145-70-0,24257-58-7,123485-24-5,123485-25-6,123485-26-7)

Guidance literature:

cis-1-phenyl-1-propylene; With magnesium(II) perchlorate hexahydrate; Fe^II(OTf)₂(tris((5-(triisopropylsilyl)pyridin-2-yl)methyl)amine); dihydrogen peroxide; In water; acetonitrile; at 20 ℃; for 1h;

acetic anhydride; In water; acetonitrile; at 0 - 20 ℃; for 0.5h; chemoselective reaction;

DOI:10.1021/jacs.7b07909

Reference yield: 57.0%

1-propenylbenzene (873-66-5) + acetic anhydride (108-24-7) → (1SR,2SR)-1-phenylpropane-1,2-diyl diacetate (21145-69-7,21145-70-0,24257-58-7,123485-24-5,123485-25-6,123485-26-7) + (1RS,2SR)-1-phenylpropane-1,2-diyl diacetate (21145-69-7,21145-70-0,24257-58-7,123485-24-5,123485-25-6,123485-26-7)

Guidance literature:

With 2,2':6,2''-terpyridine; oxygen; palladium diacetate; acetic acid; bis(pinacol)diborane; In acetonitrile; at 90 ℃; for 24h; under 760.051 Torr; diastereoselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.8b01806

Reference yield: 57.0%

1-propenylbenzene (873-66-5) + acetic anhydride (108-24-7) → (1SR,2SR)-1-phenylpropane-1,2-diyl diacetate (21145-69-7,21145-70-0,24257-58-7,123485-24-5,123485-25-6,123485-26-7) + (1RS,2SR)-1-phenylpropane-1,2-diyl diacetate (21145-69-7,21145-70-0,24257-58-7,123485-24-5,123485-25-6,123485-26-7)

Guidance literature:

With 2,2':6,2''-terpyridine; oxygen; palladium diacetate; acetic acid; bis(pinacol)diborane; In acetonitrile; at 90 ℃; for 24h; under 760.051 Torr; diastereoselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.8b01806

upstream raw materials:

(±)-erythro-2-bromo-1-phenylpropyl acetate

silver(I) acetate

syn-1-phenylpropane-1,2-diol

acetic anhydride

Downstream raw materials:

(1RS,2SR)-1-phenylpropane-1,2-diol

Refernces

• 1、 Huang, Jiuzhong,Ouyang, Lu,Li, Jianxiao,Zheng, Jia,Yan, Wuxin,Wu, Wanqing,Jiang, Huanfeng. "B2pin2-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O2 as Oxygen Source and Sole Oxidant". supporting information. p. 5090 - 5093. Retrieved 2018/09/12.
• 2、 Dobson, Peter,Norman, Julie A.,Thomas, C. Barry. "The Role of Copper(II) Salts in the Oxidation of Aryl-substituted Alkenes by Peroxydisulphate Anion". . p. 1209 - 1214. Retrieved 2007/10/02.