tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate

Base Information

• Chemical Name: tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate
• CAS No.: 83945-71-5
• Molecular Formula: C₁₄H₂₀O₃
• Molecular Weight: 236.311
• Mol file: 83945-71-5.mol

Synonyms:tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate

Chemical Property of tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate

There total 4 articles about tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate 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-Butyl acrylate (1663-39-4,25232-27-3) + benzaldehyde (100-52-7) → t-butyl(2R,3S)-(+)-2-methyl-3-hydroxy-3-phenylpropionate (83945-70-4) + tert-butyl (2S,3R)-(+)-2-methyl-3-hydroxy-3-phenylpropionate (127471-66-3) + tert-butyl (2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoate (149341-21-9) + tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate (83945-71-5)

Guidance literature:

With dimethyl(ethoxy)silane; (S,S)-Rh(Phebox-bn)(OAc)2; In toluene; at 50 ℃; for 0.5h; Further Variations:; Catalysts; Reagents; Product distribution;

DOI:10.1021/ja050698m

Reference yield:

C27H47BO2 + benzaldehyde (100-52-7) → t-butyl(2R,3S)-(+)-2-methyl-3-hydroxy-3-phenylpropionate (83945-70-4) + tert-butyl (2S,3R)-(+)-2-methyl-3-hydroxy-3-phenylpropionate (127471-66-3) + tert-butyl (2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoate (149341-21-9) + tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate (83945-71-5)

Guidance literature:

C₂₇H₄₇BO₂; benzaldehyde; In diethyl ether; at -78 ℃; for 12h; Inert atmosphere;

With dihydrogen peroxide; In methanol; diethyl ether; at 20 ℃; for 6h; Solvent; Overall yield = 79 %; Overall yield = 40 mg; Inert atmosphere;

DOI:10.1021/ol401679g

Reference yield:

tert-butyl propionate (20487-40-5) + benzaldehyde (100-52-7) → t-butyl(2R,3S)-(+)-2-methyl-3-hydroxy-3-phenylpropionate (83945-70-4) + tert-butyl (2S,3R)-(+)-2-methyl-3-hydroxy-3-phenylpropionate (127471-66-3) + tert-butyl (2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoate (149341-21-9) + tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate (83945-71-5)

Guidance literature:

With chiral bromoborane ⁽¹⁾; triethylamine; In hexane; toluene; at -78 ℃; Product distribution; Mechanism; other solvents, other amine, other reaction temp., var. propionate esters and aldehydes;

DOI:10.1021/ja00168a062

upstream raw materials:

tert-butyl propionate

benzaldehyde

tert-Butyl acrylate