N-BOC-3-CHLORO-D-TYROSINE

Base Information

• Chemical Name: N-BOC-3-CHLORO-D-TYROSINE
• CAS No.: 478183-57-2
• Molecular Formula: C14H18ClNO5
• Molecular Weight: 315.754
• Hs Code.: 2924299090
• Mol file: 478183-57-2.mol

Synonyms:(R)-2-(tert-butoxycarbonylamino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid;Boc-3-chloro-D-Tyr-OH·DCHA

Chemical Property of N-BOC-3-CHLORO-D-TYROSINE

Chemical Property:

• Vapor Pressure: 1.94E-10mmHg at 25°C
• Refractive Index: 1.559
• Boiling Point: 490.6°Cat760mmHg
• Flash Point: 250.5°C
• PSA: 95.86000
• Density: 1.321g/cm³
• LogP: 2.95690
• Storage Temp.: Store at?0-5°C

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-2-((tert-Butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-BOC-3-CHLORO-D-TYROSINE

There total 3 articles about N-BOC-3-CHLORO-D-TYROSINE 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R)-1-carboxy-2-(3-chloro-4-hydroxy-phenyl)-ethyl-ammonium chloride → (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-hydroxyphenyl)propanoic acid (478183-57-2)

Guidance literature:

With sodium hydroxide; In water; tert-butyl alcohol; at 20 ℃; for 16h;

DOI:10.1021/ol0609356

Reference yield: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-chloro-D-tyrosine (162599-96-4) → (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-hydroxyphenyl)propanoic acid (478183-57-2)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 4h; Ambient temperature;

DOI:10.1021/ja00114a011

Reference yield:

tyrosine (556-02-5,18875-48-4,25619-78-7,30704-25-7) → (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-hydroxyphenyl)propanoic acid (478183-57-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / glacial acetic acid; SO₂Cl₂ / 2 h / 20 °C

2: 99 percent / NaOH / H₂O; 2-methyl-propan-2-ol / 16 h / 20 °C

With sodium hydroxide; sulfuryl dichloride; acetic acid; In water; tert-butyl alcohol;

DOI:10.1021/ol0609356

upstream raw materials:

di-tert-butyl dicarbonate

3-chloro-D-tyrosine

tyrosine

Downstream raw materials:

methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-methoxyphenyl)propanoate

methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate

(2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid

allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate

Refernces

• 1、 McCubbin, J. Adam,Maddess, Matthew L.,Lautens, Mark. "Total synthesis of cryptophycin analogues via a scaffold approach". . p. 2993 - 2996. Retrieved 2007/10/03.