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

Base Information

• Chemical Name: (S)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS No.: 1006696-27-0
• Molecular Formula: C₁₆H₂₃BO₄
• Molecular Weight: 290.167
• Mol file: 1006696-27-0.mol

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

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

There total 10 articles about (S)-methyl 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%

bis(pinacol)diborane (73183-34-3) + methyl cinnamate (103-26-4,1754-62-7) → (R)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (364634-27-5) + (S)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-27-0,364634-27-5)

Guidance literature:

With C₃₄H₂₅N₂⁽¹⁺⁾*Cl^(1-); copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 20 ℃; Reagent/catalyst; enantioselective reaction;

Reference yield: 99.0%

methyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate → (S)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-27-0,364634-27-5)

Guidance literature:

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

DOI:10.1002/adsc.201900161

Reference yield: 95.0%

Methyl cinnamate (103-26-4,1754-62-7) + bis(pinacol)diborane (73183-34-3) → (S)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-27-0,364634-27-5)

Guidance literature:

With ethanol; C₄₄H₃₀F₅N₂P; potassium tert-butylate; copper(l) chloride; In toluene; at 20 ℃; for 24h; Reagent/catalyst; Solvent; Temperature; enantioselective reaction; Catalytic behavior; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.202102642

upstream raw materials:

Methyl cinnamate

bis(pinacol)diborane

methyl cinnamate

phenylacetylene

Downstream raw materials:

methyl (S)-3-hydroxy-3-phenylpropionate