7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene

Base Information

• Chemical Name: 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene
• CAS No.: 251322-18-6
• Molecular Formula: C₄₇H₇₆O₈Si
• Molecular Weight: 797.201
• Mol file: 251322-18-6.mol

Synonyms:

Chemical Property of 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene

There total 15 articles about 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene 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:

triethylene glycol monobenzyl ether (55489-58-2,1201808-31-2) + Trifluoro-methanesulfonic acid 6-[(7R,8R,9S,13S,14S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-3-(2-methoxy-ethoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-hexyl ester → 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene (251322-18-6)

Guidance literature:

With 15-crown-5; sodium hydride; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/jo990641g

Reference yield:

6-iodohex-1-ene (18922-04-8) → 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene (251322-18-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: t-BuOK; BEt₃ / tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / 20 °C

1.2: 53 percent / t-BuOK / tetrahydrofuran; 1,2-dimethoxy-ethane / 20 °C

2.1: 76 percent / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

3.1: 98 percent / imidazole / dimethylformamide / 0 °C

4.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C

5.1: 100 percent / NaH / tetrahydrofuran / 0 - 20 °C

6.1: 9-BBN / tetrahydrofuran / 24 h

6.2: 82 percent / KOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

8.1: 51.5 mg / NaH; 15-crown-5 / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; 9-borabicyclo[3.3.1]nonane dimer; 15-crown-5; triethyl borane; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 3.1: silylation / 4.1: desilylation / 5.1: Etherification / 6.1: hydroboration / 6.2: Oxidation / 7.1: Esterification / 8.1: Etherification;

DOI:10.1021/jo990641g

Reference yield:

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene (3589-91-1) → 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene (251322-18-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-BuLi; diisopropylamine; t-BuOK / hexane; tetrahydrofuran / 3 h / -78 °C

1.2: trimethyl borate / tetrahydrofuran; hexane / 2 h / 0 °C

1.3: 93 percent / H₂O₂ / tetrahydrofuran; hexane; H₂O / 1 h / 20 °C

2.1: 83 percent / PCC / CH₂Cl₂ / 1.5 h / 20 °C

3.1: t-BuOK; BEt₃ / tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / 20 °C

3.2: 53 percent / t-BuOK / tetrahydrofuran; 1,2-dimethoxy-ethane / 20 °C

4.1: 76 percent / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

5.1: 98 percent / imidazole / dimethylformamide / 0 °C

6.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C

7.1: 100 percent / NaH / tetrahydrofuran / 0 - 20 °C

8.1: 9-BBN / tetrahydrofuran / 24 h

8.2: 82 percent / KOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 51.5 mg / NaH; 15-crown-5 / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 15-crown-5; triethyl borane; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: boronation / 1.3: Oxidation / 2.1: Oxidation / 3.1: Metallation / 3.2: Alkylation / 4.1: Reduction / 5.1: silylation / 6.1: desilylation / 7.1: Etherification / 8.1: hydroboration / 8.2: Oxidation / 9.1: Esterification / 10.1: Etherification;

DOI:10.1021/jo990641g

upstream raw materials:

triethylene glycol monobenzyl ether

6-iodohex-1-ene

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene

6-Bromo-1-hexene