1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene

Base Information

• Chemical Name: 1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene
• CAS No.: 1147862-00-7
• Molecular Formula: C₁₈H₃₆O₂Si₂
• Molecular Weight: 340.654
• Mol file: 1147862-00-7.mol

Synonyms:1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene

Chemical Property of 1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene

There total 1 articles about 1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene 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%

1,3-O-bis(tert-butyldimethylsilyl)resorcinol (120951-86-2) → 1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene (1147862-00-7)

Guidance literature:

With ammonia; lithium; tert-butyl alcohol; In tetrahydrofuran; at -78 ℃; for 1h; Reflux;

DOI:10.1021/acs.orglett.9b00486

Reference yield:

1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene (1147862-00-7) → (1S,3aS,5S,7R,9aR)-1-(2-hydroxypropan-2-yl)-7-methoxy-3a-methyl-8-oxo-1,2,3,3a,5,6,7,8,9,9a-decahydrocyclopenta[b]chromen-5-yl 4-bromobenzoate

Guidance literature:

Multi-step reaction with 7 steps

1: disodium ethylenediamine tetraacetic acid; oxone||potassium monopersulfate triple salt; methanol; Shi's ketone; potassium carbonate; sodium tetraborate / acetonitrile; water / 0.67 h / 0 °C

2: t-butyldimethylsiyl triflate / tetrahydrofuran; aq. phosphate buffer / 3 h / -78 °C / Inert atmosphere

3: piperdinium acetate / diethyl ether / 20 °C / Molecular sieve; Inert atmosphere

4: Crabtree's catalyst; hydrogen / dichloromethane / 3 h / 20 °C

5: silver(l) oxide / diethyl ether / 9 h / Molecular sieve; Inert atmosphere; Reflux

6: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C

7: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 12 h / 20 °C / Inert atmosphere

With hydrogenchloride; methanol; Shi's ketone; sodium tetraborate; Crabtree's catalyst; oxone||potassium monopersulfate triple salt; t-butyldimethylsiyl triflate; hydrogen; piperdinium acetate; potassium carbonate; disodium ethylenediamine tetraacetic acid; triphenylphosphine; silver(l) oxide; diethylazodicarboxylate; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; dichloromethane; water; toluene; acetonitrile; 7: |Mitsunobu Displacement;

DOI:10.1021/acs.orglett.9b00486

Reference yield:

1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene (1147862-00-7) → (1S,3aS,5S,7R,9aR)-7-methoxy-3a-methyl-8-oxo-1-(prop-1-en-2-yl)-1,2,3,3a,5,6,7,8,9,9a-decahydrocyclopenta[b]chromen-5-yl 4-bromobenzoate

Guidance literature:

Multi-step reaction with 8 steps

1: disodium ethylenediamine tetraacetic acid; oxone||potassium monopersulfate triple salt; methanol; Shi's ketone; potassium carbonate; sodium tetraborate / acetonitrile; water / 0.67 h / 0 °C

2: t-butyldimethylsiyl triflate / tetrahydrofuran; aq. phosphate buffer / 3 h / -78 °C / Inert atmosphere

3: piperdinium acetate / diethyl ether / 20 °C / Molecular sieve; Inert atmosphere

4: Crabtree's catalyst; hydrogen / dichloromethane / 3 h / 20 °C

5: silver(l) oxide / diethyl ether / 9 h / Molecular sieve; Inert atmosphere; Reflux

6: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C

7: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 12 h / 20 °C / Inert atmosphere

8: Burgess Reagent / benzene / 2 h / 60 °C

With hydrogenchloride; methanol; Shi's ketone; sodium tetraborate; Burgess Reagent; Crabtree's catalyst; oxone||potassium monopersulfate triple salt; t-butyldimethylsiyl triflate; hydrogen; piperdinium acetate; potassium carbonate; disodium ethylenediamine tetraacetic acid; triphenylphosphine; silver(l) oxide; diethylazodicarboxylate; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; dichloromethane; water; toluene; acetonitrile; benzene; 7: |Mitsunobu Displacement;

DOI:10.1021/acs.orglett.9b00486

upstream raw materials:

1,3-O-bis(tert-butyldimethylsilyl)resorcinol

Downstream raw materials:

(1R,3R,4R,6R)-4,6-bis(tert-butyldimethylsilyloxy)cyclohexane-1,3-diol

C₁₈H₃₇IO₃Si₂

C₂₉H₅₁BrO₈Si₂

C₂₅H₄₆O₆SSi₂