ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Base Information

• Chemical Name: ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS No.: 1006696-15-6
• Molecular Formula: C₁₇H₂₅BO₄
• Molecular Weight: 304.194
• Mol file: 1006696-15-6.mol

Synonyms:ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Chemical Property of ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

There total 13 articles about ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate 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%

ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate (1593270-23-5) → ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-15-6)

Guidance literature:

With bis(norbornadiene)rhodium(l)tetrafluoroborate; ZhaoPhos; hydrogen; In dichloromethane; at 30 ℃; for 6h; under 38002.6 Torr; Reagent/catalyst; Solvent; enantioselective reaction; Autoclave;

DOI:10.1002/adsc.201900161

Reference yield: 86.0%

bis(pinacol)diborane (73183-34-3) + ethyl cinnamate (4192-77-2) → ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-15-6)

Guidance literature:

With Rh(Phebox-sb); sodium t-butanolate; In toluene; at 80 ℃; for 0.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/b915759j

Reference yield: 77.0%

(Z)-ethyl cinnamate (4610-69-9) + bis(pinacol)diborane (73183-34-3) → ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-15-6)

Guidance literature:

With Rh(Phebox-ip); sodium t-butanolate; In toluene; at 80 ℃; for 0.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/b915759j

upstream raw materials:

bis(pinacol)diborane

ethyl cinnamate

(Z)-ethyl cinnamate

ethyl 3-phenyl-2-propenoate

Downstream raw materials:

ethyl (3R)-3-hydroxy-3-phenylpropionate

(4S,5R)-4,5-diphenyldihydrofuran-2(3H)-one

(4R,5S)-4,5-diphenyldihydrofuran-2(3H)-one

4-((2R,3R)-5-oxo-3-phenyltetrahydrofuran-2-yl)benzonitrile