Methanesulfonic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
• CAS No.: 104419-60-5
• Molecular Formula: C₃₂H₅₄O₆S
• Molecular Weight: 566.843

Synonyms:

Chemical Property of Methanesulfonic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

There total 17 articles about Methanesulfonic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl 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:

(20S)-3α,5-cyclo-20-formyl-6β-methoxy-5α-pregnane (32249-55-1) → Methanesulfonic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester (104419-60-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) lithium diisopropylamide; 2.) potassium carbonate / 1.) THF, -78 deg C, 1 h; 2.) DMF, 100 deg C, 2 h, 50 deg C, 10 min

2: 76 percent / thionyl chloride, pyridine / 0.17 h / 0 °C

3: 69 percent / DBU / benzene / 0.25 h / Heating

4: 92 percent / hydrogen / 5 percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr

5: 99 percent / lithium aluminum hydride / tetrahydrofuran / 0.5 h / Ambient temperature

6: triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

7: 81 percent / lithium aluminum hydride / diethyl ether / 0.5 h / Ambient temperature

8: pyridine / 4-(N,N-dimethylamino)pyridine / 6 h / Ambient temperature

9: p-toluenesulfonic acid / dioxane; H₂O / 1 h / 80 °C

10: 85 percent / pyridine / 4-(N,N-dimethylamino)pyridine / 8 h / Ambient temperature

11: 97 percent / 5 percent KOH / methanol / 1 h / Heating

12: 170 mg / p-toluenesulfonic acid / 2 h / Ambient temperature

13: 186 mg / pyridine / 1 h / Ambient temperature

14: 1.) BH₃-THF, 10 percent sodium hydroxide, 30 percent hydrogen peroxide; 2.) pyridinium chlorochromate / 1.) THF, 2 h, room temperature, water, 20 min; 2.) dichloromethane, room temperature, 2 h

With pyridine; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; borane-THF; hydrogen; dihydrogen peroxide; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; dmap; Rh/Al₂O₃; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1021/ja00282a034

Reference yield:

4-hydroxy-3-isopropyl-5H-furan-2-one (104336-33-6) → Methanesulfonic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester (104419-60-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) lithium diisopropylamide; 2.) potassium carbonate / 1.) THF, -78 deg C, 1 h; 2.) DMF, 100 deg C, 2 h, 50 deg C, 10 min

2: 76 percent / thionyl chloride, pyridine / 0.17 h / 0 °C

3: 69 percent / DBU / benzene / 0.25 h / Heating

4: 92 percent / hydrogen / 5 percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr

5: 99 percent / lithium aluminum hydride / tetrahydrofuran / 0.5 h / Ambient temperature

6: triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

7: 81 percent / lithium aluminum hydride / diethyl ether / 0.5 h / Ambient temperature

8: pyridine / 4-(N,N-dimethylamino)pyridine / 6 h / Ambient temperature

9: p-toluenesulfonic acid / dioxane; H₂O / 1 h / 80 °C

10: 85 percent / pyridine / 4-(N,N-dimethylamino)pyridine / 8 h / Ambient temperature

11: 97 percent / 5 percent KOH / methanol / 1 h / Heating

12: 170 mg / p-toluenesulfonic acid / 2 h / Ambient temperature

13: 186 mg / pyridine / 1 h / Ambient temperature

14: 1.) BH₃-THF, 10 percent sodium hydroxide, 30 percent hydrogen peroxide; 2.) pyridinium chlorochromate / 1.) THF, 2 h, room temperature, water, 20 min; 2.) dichloromethane, room temperature, 2 h

With pyridine; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; borane-THF; hydrogen; dihydrogen peroxide; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; dmap; Rh/Al₂O₃; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1021/ja00282a034

Reference yield:

(20R,22R)-20-hydroxy-23-methoxymethoxy-6β-methoxy-3α,5-cyclo-5α-ergost-23-eno-28,22-lactone (104336-36-9) → Methanesulfonic acid (3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester (104419-60-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 76 percent / thionyl chloride, pyridine / 0.17 h / 0 °C

2: 69 percent / DBU / benzene / 0.25 h / Heating

3: 92 percent / hydrogen / 5 percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr

4: 99 percent / lithium aluminum hydride / tetrahydrofuran / 0.5 h / Ambient temperature

5: triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

6: 81 percent / lithium aluminum hydride / diethyl ether / 0.5 h / Ambient temperature

7: pyridine / 4-(N,N-dimethylamino)pyridine / 6 h / Ambient temperature

8: p-toluenesulfonic acid / dioxane; H₂O / 1 h / 80 °C

9: 85 percent / pyridine / 4-(N,N-dimethylamino)pyridine / 8 h / Ambient temperature

10: 97 percent / 5 percent KOH / methanol / 1 h / Heating

11: 170 mg / p-toluenesulfonic acid / 2 h / Ambient temperature

12: 186 mg / pyridine / 1 h / Ambient temperature

13: 1.) BH₃-THF, 10 percent sodium hydroxide, 30 percent hydrogen peroxide; 2.) pyridinium chlorochromate / 1.) THF, 2 h, room temperature, water, 20 min; 2.) dichloromethane, room temperature, 2 h

With pyridine; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; borane-THF; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; dmap; Rh/Al₂O₃; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1021/ja00282a034

upstream raw materials:

Methanesulfonic acid (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-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-yl ester

(20S)-3α,5-cyclo-20-formyl-6β-methoxy-5α-pregnane

4-hydroxy-3-isopropyl-5H-furan-2-one

(3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-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

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