tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

Base Information

• Chemical Name: tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate
• CAS No.: 148903-85-9
• Molecular Formula: C₁₇H₂₅NO₄
• Molecular Weight: 307.39
• Mol file: 148903-85-9.mol

Synonyms:tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

Chemical Property of tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

There total 12 articles about tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate 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: 56.0%

di-tert-butyl dicarbonate (24424-99-5) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate (148903-85-9)

Guidance literature:

(1S,2S)-2-amino-1-phenyl-1,3-diol; In acetone; toluene; for 24h; Inert atmosphere; Dean-Stark; Reflux;

di-tert-butyl dicarbonate; In tetrahydrofuran; acetone; toluene; at 20 ℃; for 16h; Inert atmosphere; Dean-Stark;

DOI:10.1002/chem.201604616

Reference yield:

(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester → tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate (148903-85-9)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1055/s-1998-3132

Reference yield:

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate (148903-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol / 0.5 h

2: imidazole / dimethylformamide / 13.5 h / 20 - 60 °C

3: p-TsOH / benzene / 0.5 h / Heating

4: tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 50 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0960-894X(02)00888-0

upstream raw materials:

di-tert-butyl dicarbonate

(1S,2S)-2-amino-1-phenyl-1,3-diol

acetone

tert-butyl [(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]carbamate

Downstream raw materials:

(4R,5S)-4-Formyl-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

tert-butyl (4S,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

tert-butyl (4S,5S)-4-[(1R)-2-(diethoxyphosphoryl)-2,2-difluoro-1-hydroxyethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

(3S,4S)-1,1-difluoro-4-hydroxy-3-(palmitoylamino)-4-phenylbutylphosphonic acid