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

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl ester
• CAS No.: 91229-00-4
• Molecular Formula: C₃₇H₅₆O₄S
• Molecular Weight: 596.915
• Mol file: 91229-00-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl 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:

trans-2-methylcyclopropanecarboxylic acid chloride (42274-66-8,52194-64-6,52194-65-7,60733-34-8) → Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl ester (91229-00-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.9 g / 2.4 M n-butyllithium / tetrahydrofuran / 0 °C

2: 77 percent / benzene / 10 h / Heating

3: 80 percent / 0.55 M NaBH₄ / pyridine / 4 h

4: 94 percent / 2.4 M n-butyllithium / tetrahydrofuran / 4 h / 0 °C

5: 1.) 1 M borane; 2.) 30 percent H₂O₂, dild. NaOH / 1.) THF, 0 deg C, 2h

6: pyridine / 24 h

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; borane; dihydrogen peroxide; In tetrahydrofuran; pyridine; benzene;

DOI:10.1021/ja00331a035

Reference yield:

triphenylphopshoranilidenemethyl (2'-methyl)cyclopropyl ketone (91228-92-1) → Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl ester (91229-00-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / benzene / 10 h / Heating

2: 80 percent / 0.55 M NaBH₄ / pyridine / 4 h

3: 94 percent / 2.4 M n-butyllithium / tetrahydrofuran / 4 h / 0 °C

4: 1.) 1 M borane; 2.) 30 percent H₂O₂, dild. NaOH / 1.) THF, 0 deg C, 2h

5: pyridine / 24 h

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; borane; dihydrogen peroxide; In tetrahydrofuran; pyridine; benzene;

DOI:10.1021/ja00331a035

Reference yield:

(25RS,26RS)-24-methylene-26-methyl-6β-methoxy-3α,5:25,27-dicyclo-5α-cholestane → Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl ester (91229-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 1 M borane; 2.) 30 percent H₂O₂, dild. NaOH / 1.) THF, 0 deg C, 2h

2: pyridine / 24 h

With sodium hydroxide; borane; dihydrogen peroxide; In pyridine;

DOI:10.1021/ja00331a035

upstream raw materials:

p-toluenesulfonyl chloride

(24R,25R,26R)-24-hydroxymethyl-26-methyl-6β-methoxy-3α,5:25,27-dicyclo-5α-cholestane

trans-2-methylcyclopropanecarboxylic acid chloride

triphenylphopshoranilidenemethyl (2'-methyl)cyclopropyl ketone

Downstream raw materials:

(24R,25R,26R)-petrosterol

Refernces