Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-cyclohexyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-cyclohexyl ester
• CAS No.: 184886-40-6
• Molecular Formula: C₁₄H₂₈O₁₀S
• Molecular Weight: 388.436
• Mol file: 184886-40-6.mol

Synonyms:Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-cyclohexyl ester

Chemical Property of Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-cyclohexyl ester

There total 12 articles about Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-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:

C13H19BrO5 (146830-40-2) → Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-cyclohexyl ester (184886-40-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / iPr₂EtN / CH₂Cl₂

2: 79 percent / Zn, AcOH / ethanol

3: 86 percent / NaHCO₃ / diphenyl ether / 0.5 h / 260 °C

4: Et₃N, DMAP / CH₂Cl₂ / 0 °C

5: Bu₃SnH, AIBN / benzene / 80 °C

6: 30percent H₂O₂, KHCO₃ / methanol; tetrahydrofuran / Heating

7: 100 percent / imidazole / dimethylformamide

8: iPrEtN, DMAP / CH₂Cl₂

9: TBAF / tetrahydrofuran

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1246/cl.1996.987

Reference yield:

C13H17BrO3 (146830-39-9) → Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-cyclohexyl ester (184886-40-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / OsO₄, N-methylmorpholine N-oxide / tetrahydrofuran; H₂O

2: 97 percent / iPr₂EtN / CH₂Cl₂

3: 79 percent / Zn, AcOH / ethanol

4: 86 percent / NaHCO₃ / diphenyl ether / 0.5 h / 260 °C

5: Et₃N, DMAP / CH₂Cl₂ / 0 °C

6: Bu₃SnH, AIBN / benzene / 80 °C

7: 30percent H₂O₂, KHCO₃ / methanol; tetrahydrofuran / Heating

8: 100 percent / imidazole / dimethylformamide

9: iPrEtN, DMAP / CH₂Cl₂

10: TBAF / tetrahydrofuran

With 1H-imidazole; dmap; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1246/cl.1996.987

Reference yield:

Acetic acid (1S,4R,4aS,5R,8S,8aR)-8-methoxymethoxy-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-yl ester (146830-37-7) → Methanesulfonic acid (1S,2S,3S,4R,6R)-6-hydroxymethyl-2,3,4-tris-methoxymethoxy-cyclohexyl ester (184886-40-6)

Guidance literature:

Multi-step reaction with 12 steps

1: K₂CO₃ / methanol

2: NBS / CH₂Cl₂

3: 86 percent / OsO₄, N-methylmorpholine N-oxide / tetrahydrofuran; H₂O

4: 97 percent / iPr₂EtN / CH₂Cl₂

5: 79 percent / Zn, AcOH / ethanol

6: 86 percent / NaHCO₃ / diphenyl ether / 0.5 h / 260 °C

7: Et₃N, DMAP / CH₂Cl₂ / 0 °C

8: Bu₃SnH, AIBN / benzene / 80 °C

9: 30percent H₂O₂, KHCO₃ / methanol; tetrahydrofuran / Heating

10: 100 percent / imidazole / dimethylformamide

11: iPrEtN, DMAP / CH₂Cl₂

12: TBAF / tetrahydrofuran

With 1H-imidazole; dmap; N-Bromosuccinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium carbonate; potassium hydrogencarbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1246/cl.1996.987

upstream raw materials:

C₁₃H₁₉BrO₅

C₁₃H₁₇BrO₃

Acetic acid (1S,4R,4aS,5R,8S,8aR)-8-methoxymethoxy-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-yl ester

C₁₇H₂₇BrO₇

Downstream raw materials:

shikimic acid

methyl shikimate

methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate