tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate

Base Information

• Chemical Name: tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate
• CAS No.: 1290617-49-0
• Molecular Formula: C₂₆H₂₅FN₂O₄
• Molecular Weight: 448.494
• Mol file: 1290617-49-0.mol

Synonyms:tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate

Chemical Property of tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate

There total 4 articles about tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate 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:

6-fluoro-2-nitrobenzoic acid (385-02-4) → tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate (1290617-49-0) + tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-D-phenylalaninate

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate; boron trifluoride dimethyl etherate / tetrahydrofuran / 0 - 20 °C

2: carbon tetrabromide; triphenylphosphine / dichloromethane / 2 h / 20 °C

3: caesium hydroxide monohydrate; (-)-(O)-⁽⁹⁾-allyl-N-(9-anthracenylmethyl)cinchodinium bromide / dichloromethane / 18 h / -30 °C

With sodium tetrahydroborate; boron trifluoride dimethyl etherate; (-)-(O)-⁽⁹⁾-allyl-N-(9-anthracenylmethyl)cinchodinium bromide; caesium hydroxide monohydrate; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo200530j

Reference yield:

2-(bromomethyl)-1-fluoro-3-nitrobenzene (1958-93-6) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate (1290617-49-0)

Guidance literature:

With (1S,2S,4S,5R)-2-((R)-(allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide; cesiumhydroxide monohydrate; In dichloromethane; at -30 ℃; for 18h;

DOI:10.1021/ml200204m

Reference yield:

2-(bromomethyl)-1-fluoro-3-nitrobenzene (1958-93-6) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-L-phenylalaninate (1290617-49-0) + tert-butyl N-(diphenylmethylidene)-2-fluoro-6-nitro-D-phenylalaninate

Guidance literature:

With (-)-(O)-⁽⁹⁾-allyl-N-(9-anthracenylmethyl)cinchodinium bromide; caesium hydroxide monohydrate; In dichloromethane; at -30 ℃; for 18h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/jo200530j

upstream raw materials:

2-(bromomethyl)-1-fluoro-3-nitrobenzene

N-(diphenylmethylene)glycine tert-butyl ester

(2-fluoro-6-nitrophenyl)methanol

6-fluoro-2-nitrobenzoic acid