(22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate

Base Information

• Chemical Name: (22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate
• CAS No.: 83066-70-0
• Molecular Formula: C₃₂H₅₄O₆S
• Molecular Weight: 566.843
• Mol file: 83066-70-0.mol

Synonyms:(22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate

Chemical Property of (22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate

There total 23 articles about (22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate 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:

3-methyl-but-1-yne (598-23-2) → (22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate (83066-70-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) n-BuLi / 1.) THF, room temperature, 30 min, 2.) -78 deg C, 1.5 h

2: 1.) MeSO₂X, 2.) potassium superoxide, 18-crown-6 / 2.) DMF, DMSO

3: 3.4 g / H₂ / Lindlar catalyst / diethyl ether; ethanol / 3 h

4: 85 percent / 70percent t-butyl hydroperoxide, vanadyloxy acetylacetonate / benzene / 2.5 h / Ambient temperature

5: 1.)Et₃Al, 2.) 2M HCl / 1.) THF, hexane, 0 deg C, 16 h, 2.) MeOH, THF, room temperature, 1 h

6: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature

7: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature

8: 580 mg / pyridine / 16 h / Ambient temperature

9: NaBH₄ / methanol; tetrahydrofuran / 3 h / Ambient temperature

10: 260 mg / pyridine / 3 h / Ambient temperature

11: 96 percent / NaI / acetone / 72 h / Heating

12: 98 percent / Bu₃SnH / tetrahydrofuran / 18 h / Ambient temperature

13: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature

14: pyridine / 2 h / Ambient temperature

15: 1.) BF₃-THF complex, 2.) 2N NaOH, 30percent H₂O₂, 3.) pyridinium chloroformate

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; potassium superoxide; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; boron trifluoride-tetrahydrofuran complex; bis(acetylacetonate)oxovanadium; pyridinium chloroformate; 18-crown-6 ether; hydrogen; dihydrogen peroxide; triethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium iodide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; acetone; benzene;

DOI:10.1039/P19840000139

Reference yield:

3β-(tetrahydropyran-2-yloxy)-23,24-dinorchol-5-en-22-al (22145-61-5) → (22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate (83066-70-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) n-BuLi / 1.) THF, room temperature, 30 min, 2.) -78 deg C, 1.5 h

2: 1.) MeSO₂X, 2.) potassium superoxide, 18-crown-6 / 2.) DMF, DMSO

3: 3.4 g / H₂ / Lindlar catalyst / diethyl ether; ethanol / 3 h

4: 85 percent / 70percent t-butyl hydroperoxide, vanadyloxy acetylacetonate / benzene / 2.5 h / Ambient temperature

5: 1.)Et₃Al, 2.) 2M HCl / 1.) THF, hexane, 0 deg C, 16 h, 2.) MeOH, THF, room temperature, 1 h

6: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature

7: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature

8: 580 mg / pyridine / 16 h / Ambient temperature

9: NaBH₄ / methanol; tetrahydrofuran / 3 h / Ambient temperature

10: 260 mg / pyridine / 3 h / Ambient temperature

11: 96 percent / NaI / acetone / 72 h / Heating

12: 98 percent / Bu₃SnH / tetrahydrofuran / 18 h / Ambient temperature

13: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature

14: pyridine / 2 h / Ambient temperature

15: 1.) BF₃-THF complex, 2.) 2N NaOH, 30percent H₂O₂, 3.) pyridinium chloroformate

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; potassium superoxide; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; boron trifluoride-tetrahydrofuran complex; bis(acetylacetonate)oxovanadium; pyridinium chloroformate; 18-crown-6 ether; hydrogen; dihydrogen peroxide; triethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium iodide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; acetone; benzene;

DOI:10.1039/P19840000139

Reference yield:

(22S)-3β-tetrahydropyranyloxycholest-5-en-23-yn-22-ol (76976-83-5) → (22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate (83066-70-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) MeSO₂X, 2.) potassium superoxide, 18-crown-6 / 2.) DMF, DMSO

2: 3.4 g / H₂ / Lindlar catalyst / diethyl ether; ethanol / 3 h

3: 85 percent / 70percent t-butyl hydroperoxide, vanadyloxy acetylacetonate / benzene / 2.5 h / Ambient temperature

4: 1.)Et₃Al, 2.) 2M HCl / 1.) THF, hexane, 0 deg C, 16 h, 2.) MeOH, THF, room temperature, 1 h

5: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature

6: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature

7: 580 mg / pyridine / 16 h / Ambient temperature

8: NaBH₄ / methanol; tetrahydrofuran / 3 h / Ambient temperature

9: 260 mg / pyridine / 3 h / Ambient temperature

10: 96 percent / NaI / acetone / 72 h / Heating

11: 98 percent / Bu₃SnH / tetrahydrofuran / 18 h / Ambient temperature

12: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature

13: pyridine / 2 h / Ambient temperature

14: 1.) BF₃-THF complex, 2.) 2N NaOH, 30percent H₂O₂, 3.) pyridinium chloroformate

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; potassium superoxide; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex; bis(acetylacetonate)oxovanadium; pyridinium chloroformate; 18-crown-6 ether; hydrogen; dihydrogen peroxide; triethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium iodide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; acetone; benzene;

DOI:10.1039/P19840000139

upstream raw materials:

methanesulfonyl chloride

teasterone 22,23-acetonide

(22R,23R,24S)-22,23-isopropylidenedioxy-3β-methylsulphonyloxyergost-5-ene

3-methyl-but-1-yne

Downstream raw materials:

typhasterol

castasterone