(1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one

Base Information

Chemical Name:(1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one
CAS No.:952092-42-1
Molecular Formula:C₂₈H₄₄O₅Si
Molecular Weight:488.74
Hs Code.:

Synonyms:(1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one

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Chemical Property of (1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one

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Technology Process of (1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one

There total 5 articles about (1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one 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%

: 952092-41-0
(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol

: 952092-42-1
(1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one

Guidance literature:: With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; acetonitrile; for 1.5h;
DOI:10.1021/jo070862j

Reference yield:

: 895532-57-7
(1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutane

: 952092-42-1
(1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / hydrogen / Pd/C / tetrahydrofuran / 24 h / 31029.7 Torr

2.1: 100 percent / N-methylmorpholine N-oxide monohydrate; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 0.5 h

3.1: tert-butyllithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

3.2: 71 percent / tetrahydrofuran; pentane / 3 h / -78 °C

4.1: 60 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 10 h / 83 °C

5.1: 99 percent / N-methylmorpholine N-oxide monohydrate; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 1.5 h

With tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile; tert-butyl alcohol; pentane;
DOI:10.1021/jo070862j

Reference yield:

: 895532-62-4
(1R,3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[2-(methoxymethoxy)ethyl]-2,2-dimethylcyclobutanol

: 952092-42-1
(1R,5S,6R)-6-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / N-methylmorpholine N-oxide monohydrate; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 0.5 h

2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

2.2: 71 percent / tetrahydrofuran; pentane / 3 h / -78 °C

3.1: 60 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 10 h / 83 °C

4.1: 99 percent / N-methylmorpholine N-oxide monohydrate; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 1.5 h

With tetrapropylammonium perruthennate; 4 A molecular sieve; tert.-butyl lithium; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; acetonitrile; tert-butyl alcohol; pentane;
DOI:10.1021/jo070862j