(E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine

Base Information

• Chemical Name: (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine
• CAS No.: 709026-61-9
• Molecular Formula: C₁₈H₂₅NO₃
• Molecular Weight: 303.401
• Mol file: 709026-61-9.mol

Synonyms:(E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine

Chemical Property of (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine

There total 4 articles about (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine 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: 91.0%

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) + benzyltriphenylphosphonium bromide (1449-46-3) → (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine (709026-61-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.bmcl.2004.03.001

Reference yield: 84.0%

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) + triphenyl(phenylmethylene)phosphorane (16721-45-2) → (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine (709026-61-9)

Guidance literature:

In tetrahydrofuran; toluene; for 4h; Ambient temperature;

DOI:10.1021/jo00013a023

Reference yield:

benzyltriphenylphosphonium bromide (1449-46-3) → (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine (709026-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hexamethyldisilazane (KHMDS) / tetrahydrofuran; toluene / 1.) -75 deg C, 0.5 h, 2.) 0 deg C, 1 h

2: 84 percent / tetrahydrofuran; toluene / 4 h / Ambient temperature

With potassium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1021/jo00013a023

upstream raw materials:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

triphenyl(phenylmethylene)phosphorane

benzyltriphenylphosphonium bromide

benzyl bromide

Downstream raw materials:

[1-(dimethoxy-phosphoryloxymethyl)-3-phenyl-propyl]-carbamic acid tert-butyl ester

tert-butyl (R)-(1-hydroxy-4-phenylbutan-2-yl)carbamate

tert-butyl (4R)-2,2-dimethyl-4-(2-phenylethyl)-1,3-oxazolidine-3-carboxylate

(Z)-(R)-N-Boc-2-amino-4-phenyl-3-butenol