Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-yl ester

Base Information

Chemical Name:Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-yl ester
CAS No.:111619-20-6
Molecular Formula:C₂₅H₃₈O₇S
Molecular Weight:482.639
Hs Code.:

Synonyms:Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-yl ester

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Chemical Property of Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-yl ester

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Technology Process of Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-yl ester

There total 15 articles about Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-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: 96.0%

: 111596-67-9
(1R,2S,4S,5S,8R)-2-((R)-4-Benzyloxy-1-methyl-butyl)-8-methoxymethoxy-octahydro-1,5-methano-indene-4,7a-diol

: 98-59-9
p-toluenesulfonyl chloride

: 111619-20-6
Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-yl ester

Guidance literature:: With pyridine; In dichloromethane; at 24 ℃;
DOI:10.1016/S0040-4039(00)96035-0

Reference yield:

: 111596-61-3
(E)-4-[(1S,3R,4R)-1-Methoxymethoxy-5-oxo-3-((E)-propenyl)-bicyclo[2.2.2]oct-2-yl]-but-2-enoic acid methyl ester

: 111619-20-6
Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-yl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 97 percent / t-BuOK / tetrahydrofuran / -78 °C / var. temp.

2: HCl / ethanol / 25 °C

3: dl-CSA / benzene / 50 °C

4: NaBH₄

5: 93 percent / iPr₂EtN / 1,2-dichloro-ethane / 60 °C

6: 1.) LDA / 1.) THF, -78 deg C, 2.) -78 to 25 deg C

7: 1.) O₃, 2.) Me₂S

8: 1.) DIBAH / 1.) THF, -78 deg C, 2.) ClCH₂CH₂Cl, 40 deg C

9: 84 percent / H₂ / 10percent Pd/C

10: 96 percent / n-Bu₃P / pyridine / 100 °C

11: 1.) MCPBA, 2.) i-Pr₂EtN / 2.) 1,2-dichlorobenzene, 180 deg C

12: 78 percent / KH

13: 1.) O₃, 2.) Me₂S

14: 98 percent / NaBH₄

15: 96 percent / pyridine / CH₂Cl₂ / 24 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; dimethylsulfide; tributylphosphine; DL-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; potassium hydride; diisobutylaluminium hydride; ozone; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; 1,2-dichloro-ethane; benzene;
DOI:10.1016/S0040-4039(00)96035-0

Reference yield:

: 111596-77-1,113474-01-4
(E)-4-[(1S,3S,4R,5R)-5-Hydroxy-1-methoxymethoxy-3-((E)-propenyl)-bicyclo[2.2.2]oct-2-yl]-but-2-enoic acid methyl ester

: 111619-20-6
Methanesulfonic acid (1R,2S,4S,5S,8R)-2-((R)-4-benzyloxy-1-methyl-butyl)-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-4-yl ester

Guidance literature:: Multi-step reaction with 16 steps

1: 94 percent / PCC

2: 97 percent / t-BuOK / tetrahydrofuran / -78 °C / var. temp.

3: HCl / ethanol / 25 °C

4: dl-CSA / benzene / 50 °C

5: NaBH₄

6: 93 percent / iPr₂EtN / 1,2-dichloro-ethane / 60 °C

7: 1.) LDA / 1.) THF, -78 deg C, 2.) -78 to 25 deg C

8: 1.) O₃, 2.) Me₂S

9: 1.) DIBAH / 1.) THF, -78 deg C, 2.) ClCH₂CH₂Cl, 40 deg C

10: 84 percent / H₂ / 10percent Pd/C

11: 96 percent / n-Bu₃P / pyridine / 100 °C

12: 1.) MCPBA, 2.) i-Pr₂EtN / 2.) 1,2-dichlorobenzene, 180 deg C

13: 78 percent / KH

14: 1.) O₃, 2.) Me₂S

15: 98 percent / NaBH₄

16: 96 percent / pyridine / CH₂Cl₂ / 24 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; dimethylsulfide; tributylphosphine; DL-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; potassium hydride; diisobutylaluminium hydride; ozone; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; 1,2-dichloro-ethane; benzene;
DOI:10.1016/S0040-4039(00)96035-0