2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran

Base Information

Chemical Name:2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran
CAS No.:113432-71-6
Molecular Formula:C₂₉H₄₄O₅
Molecular Weight:472.665
Hs Code.:

Synonyms:2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran

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Chemical Property of 2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran

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Technology Process of 2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran

There total 19 articles about 2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran 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: 93.0%

: 110-87-2
3,4-dihydro-2H-pyran

: 113432-70-5
(1S,5S,7S,10R)-5-((R)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-ol

: 113432-71-6
2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran

Guidance literature:: With DL-10-camphorsulfonic acid;
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

: 113432-71-6
2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 19 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

17: 72 percent / NaH, 15-crown-5 / toluene / 0.08 h / 100 °C

18: 97 percent / NaBH₄

19: 93 percent / dl-CSA

With pyridine; hydrogenchloride; sodium tetrahydroborate; 15-crown-5; dimethylsulfide; tributylphosphine; DL-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; potassium hydride; sodium 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; toluene; benzene;
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

: 113432-71-6
2-[(1R,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-yloxy]-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 18 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

16: 72 percent / NaH, 15-crown-5 / toluene / 0.08 h / 100 °C

17: 97 percent / NaBH₄

18: 93 percent / dl-CSA

With pyridine; hydrogenchloride; sodium tetrahydroborate; 15-crown-5; dimethylsulfide; tributylphosphine; DL-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; potassium hydride; sodium 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; toluene; benzene;
DOI:10.1016/S0040-4039(00)96035-0