11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol

Base Information

• Chemical Name: 11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol
• CAS No.: 1372163-84-2
• Molecular Formula: C₃₅H₅₀N₄O₆
• Molecular Weight: 622.805
• Mol file: 1372163-84-2.mol

Synonyms:11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol

Chemical Property of 11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol

There total 14 articles about 11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol 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: 80.0%

11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol (1372163-83-1) + 11-azido-3,6,9-trioxa-undecanyl p-toluenesulfonate (168640-82-2) → 11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol (1372163-84-2)

Guidance literature:

11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol; 11-azido-3,6,9-trioxa-undecanyl p-toluenesulfonate; With potassium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 24h;

With sodium hydroxide; In methanol; N,N-dimethyl-formamide; at 20 ℃; for 4h;

Reference yield:

(11R,13S)-11-(4-(2-(dimethylamino)ethoxy)phenyl)-13-methyl-7,8,11,12,13,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione → 11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol (1372163-84-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic anhydride / dichloromethane / 16 h / 20 °C

2.1: sodium tetrahydroborate / methanol / 1 h / 20 °C

3.1: sodium hydroxide / methanol / 16 h / 20 °C

4.1: carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 24.5 h / 0 °C / Reflux

4.2: 3 h / Reflux

5.1: potassium carbonate / acetonitrile / 16 h / 80 °C / Inert atmosphere

With sodium tetrahydroborate; carbonochloridic acid 1-chloro-ethyl ester; acetic anhydride; potassium carbonate; sodium hydroxide; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/bc200645n

Reference yield:

C27H34O3Si → 11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol (1372163-84-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: water; acetic acid / 1.5 h / 50 - 60 °C

2.1: caesium carbonate / acetone / 16 h / 80 °C

3.1: acetic anhydride / dichloromethane / 16 h / 20 °C

4.1: sodium tetrahydroborate / methanol / 1 h / 20 °C

5.1: sodium hydroxide / methanol / 16 h / 20 °C

6.1: carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 24.5 h / 0 °C / Reflux

6.2: 3 h / Reflux

7.1: potassium carbonate / acetonitrile / 16 h / 80 °C / Inert atmosphere

With sodium tetrahydroborate; carbonochloridic acid 1-chloro-ethyl ester; water; acetic anhydride; potassium carbonate; caesium carbonate; acetic acid; sodium hydroxide; In methanol; dichloromethane; acetone; acetonitrile;

DOI:10.1021/bc200645n

upstream raw materials:

3-acetoxy-11β-[4-(2-dimethylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-17-one

11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol

11-azido-3,6,9-trioxa-undecanyl p-toluenesulfonate

tetraethylene glycol di(p-toluenesulfonate)