C₁₄H₁₇Cl₂NO₅

Base Information

• Chemical Name: C₁₄H₁₇Cl₂NO₅
• CAS No.: 1259972-62-7
• Molecular Formula: C₁₄H₁₇Cl₂NO₅
• Molecular Weight: 350.199
• Mol file: 1259972-62-7.mol

Synonyms:

Chemical Property of C₁₄H₁₇Cl₂NO₅

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

BOC-DL-TYR(3,5-CL2)-OH 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₁₄H₁₇Cl₂NO₅

There total 2 articles about C₁₄H₁₇Cl₂NO₅ 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:

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-amino-3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid (15924-16-0) → C14H17Cl2NO5 (1213365-16-2,1259972-62-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1021/acs.jnatprod.0c00441

Reference yield:

tyrosine (556-02-5,18875-48-4,25619-78-7,30704-25-7) → C14H17Cl2NO5 (1213365-16-2,1259972-62-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuryl dichloride / acetic acid / 16 h / 20 °C

2: sodium hydroxide / water; 1,4-dioxane / 18 h / 20 °C

With sulfuryl dichloride; sodium hydroxide; In 1,4-dioxane; water; acetic acid;

DOI:10.1021/acs.jnatprod.0c00441

Reference yield:

Boc-3,5-dichloro-L-tyrosine (1213365-16-2,1259972-62-7) → nannocystin A

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 8 h / 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

4.2: 2 h / 0 - 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate / dichloromethane; acetonitrile / 16 h / 20 °C / Inert atmosphere

7.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

8.1: benzotriazol-1-ol; 4-methyl-morpholine; N,N-dimethyl-formamide; diisopropyl-carbodiimide / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; silver(l) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; 1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dimethylamino)sulfonium trimethylsilyldifluoride; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); trifluoroacetic acid; silver(l) oxide; diisopropyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 9.1: |Suzuki Coupling;

DOI:10.1002/anie.201606679

upstream raw materials:

tyrosine

di-tert-butyl dicarbonate

(R)-2-amino-3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid

Downstream raw materials:

(S)-[(S)-2-Amino-3-(3,5-dichloro-4-hydroxy-phenyl)-propionylamino]-(3,5-dimethoxy-phenyl)-acetic acid methyl ester

(S)-[(S)-2-[(R)-2-Amino-2-(4-benzyloxy-phenyl)-acetylamino]-3-(3,5-dichloro-4-hydroxy-phenyl)-propionylamino]-(3,5-dimethoxy-phenyl)-acetic acid methyl ester

(S)-[(S)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-propionylamino]-(3,5-dimethoxy-phenyl)-acetic acid methyl ester