Methanesulfonic acid (1S,3S,4R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,3S,4R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexyl ester
• CAS No.: 192633-10-6
• Molecular Formula: C₂₁H₄₀O₇SSi
• Molecular Weight: 464.696
• Mol file: 192633-10-6.mol

Synonyms:

Chemical Property of Methanesulfonic acid (1S,3S,4R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1S,3S,4R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexyl ester

There total 16 articles about Methanesulfonic acid (1S,3S,4R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexyl 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:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → Methanesulfonic acid (1S,3S,4R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexyl ester (192633-10-6)

Guidance literature:

Multi-step reaction with 7 steps

1: i-Pr₂NEt

2: 1.) OsO₄, NMO; 2.) NaIO₄, NHCO₃ / 1.) CH₃CN, H₂O; 2.) 0 deg C

3: 98 percent / L-selectride / tetrahydrofuran / -78 °C

4: Na / liquid ammonia; ethanol / -34 °C

5: Bu₃P, pyridine / 60 °C

6: 1.) MCPBA; 2.) i-Pr₂NEt / 1.) CH₂Cl₂, -78 deg C; 2.) o-dichlorobenzene, 180 deg C

7: DMAP / pyridine / Ambient temperature

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tributylphosphine; sodium; L-Selectride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; ethanol; ammonia;

DOI:10.1016/S0040-4039(97)01069-1

Reference yield:

methyl (1S, 2R, 3R, 4R, 4'S)-1-methoxymethyloxy-4-methyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-oxobicyclo[2.2.2]octane-2-carboxylate (147728-68-5) → Methanesulfonic acid (1S,3S,4R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexyl ester (192633-10-6)

Guidance literature:

Multi-step reaction with 15 steps

1: LiAlH / tetrahydrofuran / Ambient temperature

2: NaH / tetrahydrofuran; dimethylformamide / 0 °C

3: PCC / Ambient temperature

4: TsOH / acetone; H₂O

5: pyridine / Ambient temperature

6: 96 percent / NaBH₄ / methanol / 0 °C

7: 81 percent / t-BuOK, / 2-methyl-propan-2-ol / 1 h / 25 °C

8: 98 percent / NaBH₄ / methanol / 0 °C

9: i-Pr₂NEt

10: 1.) OsO₄, NMO; 2.) NaIO₄, NHCO₃ / 1.) CH₃CN, H₂O; 2.) 0 deg C

11: 98 percent / L-selectride / tetrahydrofuran / -78 °C

12: Na / liquid ammonia; ethanol / -34 °C

13: Bu₃P, pyridine / 60 °C

14: 1.) MCPBA; 2.) i-Pr₂NEt / 1.) CH₂Cl₂, -78 deg C; 2.) o-dichlorobenzene, 180 deg C

15: DMAP / pyridine / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tributylphosphine; potassium tert-butylate; sodium; L-Selectride; sodium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; ethanol; ammonia; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4039(97)01069-1

Reference yield:

(1R,4S,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxymethyl-4-methoxymethoxy-1-methyl-bicyclo[2.2.2]octan-2-ol → Methanesulfonic acid (1S,3S,4R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexyl ester (192633-10-6)

Guidance literature:

Multi-step reaction with 14 steps

1: NaH / tetrahydrofuran; dimethylformamide / 0 °C

2: PCC / Ambient temperature

3: TsOH / acetone; H₂O

4: pyridine / Ambient temperature

5: 96 percent / NaBH₄ / methanol / 0 °C

6: 81 percent / t-BuOK, / 2-methyl-propan-2-ol / 1 h / 25 °C

7: 98 percent / NaBH₄ / methanol / 0 °C

8: i-Pr₂NEt

9: 1.) OsO₄, NMO; 2.) NaIO₄, NHCO₃ / 1.) CH₃CN, H₂O; 2.) 0 deg C

10: 98 percent / L-selectride / tetrahydrofuran / -78 °C

11: Na / liquid ammonia; ethanol / -34 °C

12: Bu₃P, pyridine / 60 °C

13: 1.) MCPBA; 2.) i-Pr₂NEt / 1.) CH₂Cl₂, -78 deg C; 2.) o-dichlorobenzene, 180 deg C

14: DMAP / pyridine / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tributylphosphine; potassium tert-butylate; sodium; L-Selectride; sodium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; ethanol; ammonia; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4039(97)01069-1

upstream raw materials:

methanesulfonyl chloride

(1S,3S,4R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-methylene-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-cyclohexanol

(2-trimethylethylsilylethoxy)methyl chloride

methyl (1S, 2R, 3R, 4R, 4'S)-1-methoxymethyloxy-4-methyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-oxobicyclo[2.2.2]octane-2-carboxylate