tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate

Base Information

• Chemical Name: tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate
• CAS No.: 714951-38-9
• Molecular Formula: C₂₉H₃₅NO₄
• Molecular Weight: 461.601
• Mol file: 714951-38-9.mol

Synonyms:tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate

Chemical Property of tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate

There total 1 articles about tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)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: 85.0%

tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate (53484-52-9) + (R)-N-benzyl-1-phenylethylamine (38235-77-7) → tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate (714951-38-9)

Guidance literature:

(R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

With (1R)-(?)-(10-camphorsulfonyl)oxaziridine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 14h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2014.06.057

Reference yield: 55.0%

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate (714951-38-9) → tert-butyl (2S,3S,αR)-2-[N-benzyl-N-(α-methylbenzyl)-amino]-3-hydroxy-3-(4'-methoxyphenyl)propanoate

Guidance literature:

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate; With triethylamine; Methanesulfonic anhydride; In dichloromethane; at 20 ℃; for 0.0166667h;

With water; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2014.06.057

Reference yield: 44.0%

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate (714951-38-9) → tert-butyl (2R,3S,αR)-2-[N-benzyl-N-(α-methylbenzyl)amino]-3-fluoro-3-(4-methoxyphenyl)propanoate + C29H33NO3 + C29H33NO3

Guidance literature:

With triethylamine tris(hydrogen fluoride); ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; at 20 ℃; for 2h; stereospecific reaction;

DOI:10.1021/acs.orglett.5b00880

upstream raw materials:

tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate

(R)-N-benzyl-1-phenylethylamine

Downstream raw materials:

(4R,5R)-cytoxazone

(4R,5S)-5-(hydroxymethyl)-4-(4-methoxyphenyl)-1,3-oxazolidin-2-one

(4R,5R)-4-(4-methoxyphenyl)-1,3-oxazolidine-2-one-5-carboxylic acid

tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate