1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene

Base Information

• Chemical Name: 1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene
• CAS No.: 201477-97-6
• Molecular Formula: C₃₈H₇₀O₆Si₂
• Molecular Weight: 679.141
• Mol file: 201477-97-6.mol

Synonyms:

Chemical Property of 1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene

There total 10 articles about 1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene 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: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1,4-bis((2R,4S,5S)-2,5-epoxy-4-hydroxydec-1-yloxy)benzene (1054624-54-2) → 1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene (201477-97-6)

Guidance literature:

In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jo971324h

Reference yield:

1,4-bis(allyloxy)benzene (37592-20-4) → 1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene (201477-97-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / (DHQD)2-PHAL, potassium ferricyanide, K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 15 h / 0 °C

2: 95 percent / 30percent HBr / 0.5 h / 50 °C

3: 90 percent / K₂CO₃ / methanol / 48 h / Ambient temperature

4: 75 percent / n-BuLi, BF₃*Et₂O / tetrahydrofuran; hexane / 2 h / -78 °C

5: 95 percent / LiAlH₄ / bis-(2-methoxy-ethyl) ether / 24 h / Heating

6: 79 percent / NaH / tetrahydrofuran / 24 h / 0 °C

7: K₂CO₃, K₃Fe(CN)6, NaHCO₃, K₂OsO₂(OH)4,DHQ)2PHAL / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

8: K₂CO₃ / methanol / 24 h / Ambient temperature

9: 90 percent / tetrahydrofuran / 24 h / Ambient temperature

With potassium osmate; lithium aluminium tetrahydride; n-butyllithium; K₂OsO₂(OH)4,DHQ)2PHAL; boron trifluoride diethyl etherate; hydrogen bromide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; hexane; diethylene glycol dimethyl ether; water; tert-butyl alcohol;

DOI:10.1021/jo971324h

Reference yield:

hydroquinone (123-31-9,8027-02-9) → 1,4-bis((2R,4S,5S)-2,5-epoxy-4-[(tert-butyldimethylsilyl)oxy]dec-1-yloxy)benzene (201477-97-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / K₂CO₃ / acetone / 5 h / Heating

2: 80 percent / (DHQD)2-PHAL, potassium ferricyanide, K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 15 h / 0 °C

3: 95 percent / 30percent HBr / 0.5 h / 50 °C

4: 90 percent / K₂CO₃ / methanol / 48 h / Ambient temperature

5: 75 percent / n-BuLi, BF₃*Et₂O / tetrahydrofuran; hexane / 2 h / -78 °C

6: 95 percent / LiAlH₄ / bis-(2-methoxy-ethyl) ether / 24 h / Heating

7: 79 percent / NaH / tetrahydrofuran / 24 h / 0 °C

8: K₂CO₃, K₃Fe(CN)6, NaHCO₃, K₂OsO₂(OH)4,DHQ)2PHAL / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

9: K₂CO₃ / methanol / 24 h / Ambient temperature

10: 90 percent / tetrahydrofuran / 24 h / Ambient temperature

With potassium osmate; lithium aluminium tetrahydride; n-butyllithium; K₂OsO₂(OH)4,DHQ)2PHAL; boron trifluoride diethyl etherate; hydrogen bromide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; hexane; diethylene glycol dimethyl ether; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo971324h

upstream raw materials:

tert-butyldimethylsilyl chloride

1,4-bis((2R,4S,5S)-2,5-epoxy-4-hydroxydec-1-yloxy)benzene

1,4-bis(allyloxy)benzene

hydroquinone