(1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate

Base Information

• Chemical Name: (1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate
• CAS No.: 1265883-13-3
• Molecular Formula: C₂₃H₃₄O₅Si
• Molecular Weight: 418.605

Synonyms:(1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate

Chemical Property of (1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate

There total 4 articles about (1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate 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:

C21H34O4Si (1265883-20-2) → (1S,4R,5R,7R)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate (1265883-29-1) + (1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate (1265883-13-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; toluene

1.2: -78 °C

2.1: N,N-dimethyl-aniline / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice

2.2: 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: bis(N-tert-butylsalicylaldiminato)copper(II) / toluene / 1 h / Inert atmosphere; Reflux

With bis(N-tert-butylsalicylaldiminato)copper(II); N,N-dimethyl-aniline; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/jo102033h

Reference yield:

C21H34O4Si (1265883-27-9) → (1S,4R,5R,7R)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate (1265883-29-1) + (1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate (1265883-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-aniline / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice

1.2: 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: bis(N-tert-butylsalicylaldiminato)copper(II) / toluene / 1 h / Inert atmosphere; Reflux

With bis(N-tert-butylsalicylaldiminato)copper(II); N,N-dimethyl-aniline; In dichloromethane; toluene;

DOI:10.1021/jo102033h

Reference yield:

C15H20O4 (1265883-18-8) → (1S,4R,5R,7R)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate (1265883-29-1) + (1R,4R,5R,7S)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate (1265883-13-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; toluene

2.2: -78 °C

3.1: N,N-dimethyl-aniline / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice

3.2: 0.5 h / 0 - 20 °C / Inert atmosphere

4.1: bis(N-tert-butylsalicylaldiminato)copper(II) / toluene / 1 h / Inert atmosphere; Reflux

With dmap; bis(N-tert-butylsalicylaldiminato)copper(II); N,N-dimethyl-aniline; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo102033h

upstream raw materials:

C₁₅H₂₀O₄

C₂₁H₃₄O₄Si

C₂₁H₃₄O₄Si

(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate

Downstream raw materials:

C₃₃H₄₂O₇

(R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate

(R)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)-3-((S)-hydroxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)but-3-en-2-yl benzoate

(R)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)-3-((R)-hydroxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)but-3-en-2-yl benzoate

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