O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate

Base Information

Chemical Name:O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate
CAS No.:952092-44-3
Molecular Formula:C₃₀H₃₆O₆S
Molecular Weight:524.678
Hs Code.:

Synonyms:O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate

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Chemical Property of O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate

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Technology Process of O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate

There total 7 articles about O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate 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: 81.0%

: 952092-43-2
(1R,5S,6R)-6-hydroxy-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one

: 937-63-3
p-Tolyl chlorothionoformate

: 952092-44-3
O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate

Guidance literature:: With dmap; In acetonitrile; for 48h;
DOI:10.1021/jo070862j

Reference yield:

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

: 952092-44-3
O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate

Guidance literature:: Multi-step reaction with 7 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

6.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran

7.1: 81 percent / 4-(dimethylamino)pyridine / acetonitrile / 48 h

With dmap; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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

: 952092-44-3
O-(1R,5S,6R)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-7,7-dimethyl-3-oxo-2-oxabicyclo[3.2.0]heptan-6-yl O-p-tolyl carbonothioate

Guidance literature:: Multi-step reaction with 6 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

5.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran

6.1: 81 percent / 4-(dimethylamino)pyridine / acetonitrile / 48 h

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