(+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate

Base Information

• Chemical Name: (+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate
• CAS No.: 714222-51-2
• Molecular Formula: C₂₅H₃₃NO₄Si
• Molecular Weight: 439.627
• Mol file: 714222-51-2.mol

Synonyms:(+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate

Chemical Property of (+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate

There total 1 articles about (+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate 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: 70.0%

(Z)-α-N-benzoylamino-2-butenoic acid methylester (60027-58-9) + [3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane (131362-25-9) → (+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate (714222-51-2)

Guidance literature:

(Z)-α-N-benzoylamino-2-butenoic acid methylester; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

[3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/ol049422u

Reference yield: 66.0%

(+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate (714222-51-2) → (+/-)-methyl N-benzoyl-α-formyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate (714222-54-5)

Guidance literature:

(+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate; With ozone; In dichloromethane; at -78 ℃;

With acetic acid; zinc; In dichloromethane; Heating;

DOI:10.1021/ol049422u

Reference yield:

(+/-)-methyl N-benzoyl-α-vinyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate (714222-51-2) → 2-benzoylamino-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1.1: ozone / CH₂Cl₂ / -78 °C

1.2: 66 percent / acetic acid; Zn / CH₂Cl₂ / Heating

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 5 percent / tetrahydrofuran / -78 - 20 °C

With ozone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol049422u

upstream raw materials:

(Z)-α-N-benzoylamino-2-butenoic acid methylester

[3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane

Downstream raw materials:

(+/-)-methyl N-benzoyl-α-formyl-(3'-O-tert-butyldimethylsilyl)-m-tyrosinate

(+/-)-methyl N-benzoyl-α-(E)-(2'-fluoro-2'-benzenesulfonyl)vinyl-(3''-O-tert-butyldimethylsilyl)-m-tyrosinate