Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester
CAS No.:119005-08-2
Molecular Formula:C₄₀H₅₈O₆S
Molecular Weight:666.963
Hs Code.:

Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester

Synonyms:Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester

There total 14 articles about Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl 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: 94.0%

: 119005-05-9
(20S)-6β-methoxy-25-((2'-tetrahydropyranyl)oxy)-23,24-bisdehydro-3α,5α-cyclocholestan-21-ol

: 98-59-9
p-toluenesulfonyl chloride

: 119005-08-2
Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester

Guidance literature:: With pyridine; for 16h;
DOI:10.1021/jo00298a020

Reference yield:

: 64338-43-8
[(3aR,3bS,5aS,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-tetradecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-(6E)-ylidene]-acetic acid ethyl ester

: 119005-08-2
Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: H₂ / Pt / ethanol

2: 60 percent / lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

3: 70 percent / AcOOH / tetrahydrofuran / -5 deg C then reflux

4: 95 percent / LiAlH₄ / diethyl ether

6: tri-n-butyltin hydride / AIBN

7: 77 percent / H₂O₂, KF / dimethylformamide

9: 58 percent / BF₃*Et₂O

10: pyridine

With peracetic acid; potassium fluoride; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); platinum; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)80404-9

Reference yield:

: 74348-77-9
ethyl 6β-methoxy-3α,5α-cyclopregnan-21-oate

: 119005-08-2
Toluene-4-sulfonic acid (S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-6-(tetrahydro-pyran-2-yloxy)-hept-4-ynyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 60 percent / lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

2: 70 percent / AcOOH / tetrahydrofuran / -5 deg C then reflux

3: 95 percent / LiAlH₄ / diethyl ether

5: tri-n-butyltin hydride / AIBN

6: 77 percent / H₂O₂, KF / dimethylformamide

8: 58 percent / BF₃*Et₂O

9: pyridine

With peracetic acid; potassium fluoride; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; dihydrogen peroxide; tri-n-butyl-tin hydride; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)80404-9