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

Base Information

• Chemical Name: (22R,23R,24S)-22,23-isopropylidenedioxy-3β-methylsulphonyloxyergost-5-ene
• CAS No.: 83066-68-6
• Molecular Formula: C₃₂H₅₄O₅S
• Molecular Weight: 550.844
• Mol file: 83066-68-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (22R,23R,24S)-22,23-isopropylidenedioxy-3β-methylsulphonyloxyergost-5-ene 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:

methanesulfonyl chloride (124-63-0) + (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (83066-67-5) → (22R,23R,24S)-22,23-isopropylidenedioxy-3β-methylsulphonyloxyergost-5-ene (83066-68-6)

Guidance literature:

With pyridine; for 2h; Yield given; Ambient temperature;

DOI:10.1039/P19840000139

Reference yield:

3-methyl-but-1-yne (598-23-2) → (22R,23R,24S)-22,23-isopropylidenedioxy-3β-methylsulphonyloxyergost-5-ene (83066-68-6)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; potassium superoxide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; bis(acetylacetonate)oxovanadium; 18-crown-6 ether; hydrogen; 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-3β-methylsulphonyloxyergost-5-ene (83066-68-6)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; potassium superoxide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; bis(acetylacetonate)oxovanadium; 18-crown-6 ether; hydrogen; 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

(3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

3-methyl-but-1-yne

3β-(tetrahydropyran-2-yloxy)-23,24-dinorchol-5-en-22-al

Downstream raw materials:

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

typhasterol

castasterone