2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester

Base Information

• Chemical Name: 2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester
• CAS No.: 686776-20-5
• Molecular Formula: C₂₂H₂₉NO₆S
• Molecular Weight: 435.541
• Mol file: 686776-20-5.mol

Synonyms:2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester

Chemical Property of 2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester

There total 9 articles about 2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl 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: 85.0%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + 3-tolylsulfonyloxy-4-methoxy-5-methyl benzyl bromide (686776-22-7) → 2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester (686776-20-5)

Guidance literature:

N-(diphenylmethylene)glycine tert-butyl ester; 3-tolylsulfonyloxy-4-methoxy-5-methyl benzyl bromide; With cesium hydroxide; (1S,2R,4S,5R)-2-((S)-allyloxy(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane bromide; In dichloromethane; at -78 ℃;

With acetic acid; In tetrahydrofuran;

DOI:10.1055/s-2004-817763

Reference yield:

2-(benzhydrylidene-amino)-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester → 2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester (686776-20-5)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1021/jo050408k

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 2-amino-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester (686776-20-5)

Guidance literature:

Multi-step reaction with 7 steps

1: triethylamine / CH₂Cl₂ / 4 h / -70 °C

2: 23.5 g / K₂CO₃ / acetone / 5 h / 50 °C

3: 85 percent / TiCl₄ / CH₂Cl₂ / 20 °C

4: 99 percent / NaBH₄ / tetrahydrofuran; methanol; H₂O / 1 h / 0 °C

5: 95 percent / PBr₃ / CH₂Cl₂; toluene / 20 °C

6: O-⁽⁹⁾-allyl-N-(9'-anthracenylmethyl)cinchonidium bromide; CsOH*H₂O / CH₂Cl₂ / 30 h / -78 °C

7: AcOH / tetrahydrofuran; H₂O / 2 h / 20 °C

With cesium hydroxide; sodium tetrahydroborate; phosphorus tribromide; titanium tetrachloride; potassium carbonate; acetic acid; triethylamine; (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;

DOI:10.1021/jo050408k

upstream raw materials:

N-(diphenylmethylene)glycine tert-butyl ester

3-tolylsulfonyloxy-4-methoxy-5-methyl benzyl bromide

p-toluenesulfonyl chloride

3-methylbenzene-1,2-diol

Downstream raw materials:

[(S)-2-(3-Allyloxy-4-methoxy-5-methyl-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid allyl ester

[(S)-2-(3-Allyloxy-4-methoxy-5-methyl-phenyl)-1-formyl-ethyl]-carbamic acid allyl ester

[(S)-2-(3-Hydroxy-4-methoxy-5-methyl-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid allyl ester

(S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol