Threonine, N,N-bis(phenylmethyl)-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Threonine, N,N-bis(phenylmethyl)-, 1,1-dimethylethyl ester
• CAS No.: 94226-59-2
• Molecular Formula: C₂₂H₂₉NO₃
• Molecular Weight: 355.477
• Mol file: 94226-59-2.mol

Synonyms:

Chemical Property of Threonine, N,N-bis(phenylmethyl)-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Threonine, N,N-bis(phenylmethyl)-, 1,1-dimethylethyl ester

There total 13 articles about Threonine, N,N-bis(phenylmethyl)-, 1,1-dimethylethyl ester 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: 54.0%

tert-butyl (RS,RS)-2-hydroxy-3-(N,N-dibenzylamino)-butanoate → tert-butyl (RS,RS)-2-(N,N-dibenzylamino)-3-hydroxybutanoate (94226-59-2,94226-60-5)

Guidance literature:

tert-butyl (RS,RS)-2-hydroxy-3-(N,N-dibenzylamino)-butanoate; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 - 20 ℃; for 6h;

With water; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/j.tet.2014.06.057

Reference yield: 47.0%

Dibenzyl-((Z)-2-tert-butoxy-2-trimethylsilanyloxy-vinyl)-amine (102222-41-3) + acetaldehyde (75-07-0,9002-91-9) → 2-Dibenzylamino-3-hydroxy-butyric acid tert-butyl ester (94226-59-2,94226-60-5)

Guidance literature:

With titanium tetrachloride; In dichloromethane; Product distribution; Ambient temperature; other temperature: -65 deg C, effect of reaction temperature on the diastereoselectivity and yield of the aldol condensation;

DOI:10.1016/S0040-4039(00)98679-9

Reference yield:

tert-butyl 2-(dibenzylamino)ethanoate (94226-56-9) → (2R,3S)-2-Dibenzylamino-3-hydroxy-butyric acid tert-butyl ester (94226-59-2,94226-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamide / 1.) THF, -60 deg C, 10 min, 2.) -60 deg C to RT, 1 h

2: TiCl₄ / CH₂Cl₂ / -65 °C

With lithium diisopropyl amide; titanium tetrachloride; In dichloromethane;

DOI:10.1016/S0040-4020(01)85997-4

upstream raw materials:

2-Dibenzylamino-3-oxo-butyric acid tert-butyl ester

tert-butyl 2-(dibenzylamino)ethanoate

acetaldehyde

Dibenzyl-((Z)-2-tert-butoxy-2-trimethylsilanyloxy-vinyl)-amine

Downstream raw materials:

2-Dibenzylamino-3-hydroxy-butyric acid

Refernces

• 1、 Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica,Scolastico, Carlo. "DIBENZYLAMINOACETATES AS USEFUL SYNTHETIC EQUIVALENTS OF GLYCINE IN THEi SYNTHESIS OF α-AMINO-β-HYDROXYACIDS". . p. 3671 - 3684. Retrieved 2007/10/02.
• 2、 Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica,Scolastico, Carlo. "DIASTEREOSELECTIVE SYNTHESIS OF α-AMINO-β-HYDROXYACIDS". . p. 4693 - 4696. Retrieved 2007/10/02.