thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester

Base Information

• Chemical Name: thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester
• CAS No.: 952101-35-8
• Molecular Formula: C₂₀H₂₆O₆S
• Molecular Weight: 394.489

Synonyms:thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester

Chemical Property of thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester

There total 9 articles about thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester 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: 100.0%

(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one (952101-34-7) + p-Tolyl chlorothionoformate (937-63-3) → thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester (952101-35-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 16h;

DOI:10.1021/jo070861r

Reference yield:

(4R,5R)-4-benzyloxy-2-methoxy-3,3-dimethyl-5-vinyltetrahydrofuran → thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester (952101-35-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 74 percent / BF₃*OEt₂; n-butyllithium / Cp₂ZrCl₂ / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 92 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 8.5 h

3.1: 94 percent / Grubbs' second generation catalyst / CH₂Cl₂ / 18 h

4.1: 99 percent / copper(I) iodide; TMEDA / tetrahydrofuran / 1 h / -78 °C

5.1: ozone / CH₂Cl₂; methanol / 0.08 h / -78 °C

5.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

6.1: 135 mg / sodium borohydride / CH₂Cl₂; methanol / 0.17 h / 0 °C

7.1: 98 percent / ethyldiisopropylamine; tetrabutylammonium iodide / CH₂Cl₂ / 48 h

8.1: 74 percent / hydrogen / Pd/C / tetrahydrofuran / 24 h / 25858.1 Torr

9.1: 100 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h

With pyridine; dmap; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; zirconocene dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/jo070861r

Reference yield:

(1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutanol (895532-66-8) → thiocarbonic acid [(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-3-oxo-2-oxabicyclo[4.2.0]oct-7-yl] ester p-tolyl ester (952101-35-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 8.5 h

2.1: 94 percent / Grubbs' second generation catalyst / CH₂Cl₂ / 18 h

3.1: 99 percent / copper(I) iodide; TMEDA / tetrahydrofuran / 1 h / -78 °C

4.1: ozone / CH₂Cl₂; methanol / 0.08 h / -78 °C

4.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

5.1: 135 mg / sodium borohydride / CH₂Cl₂; methanol / 0.17 h / 0 °C

6.1: 98 percent / ethyldiisopropylamine; tetrabutylammonium iodide / CH₂Cl₂ / 48 h

7.1: 74 percent / hydrogen / Pd/C / tetrahydrofuran / 24 h / 25858.1 Torr

8.1: 100 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h

With pyridine; dmap; sodium tetrahydroborate; copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; hydrogen; tetra-(n-butyl)ammonium iodide; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo070861r

upstream raw materials:

(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one

p-Tolyl chlorothionoformate

(1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutanol

acrylic acid (1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutyl ester

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