(1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

Base Information

Chemical Name:(1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene
CAS No.:359887-06-2
Molecular Formula:C₂₅H₃₂O₅
Molecular Weight:412.526
Hs Code.:

Synonyms:(1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

Suppliers and Price of (1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

There total 11 articles about (1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene 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: 47.0%

: 7322-88-5
(S)-acetylmandelic acid

: rel-(1R,6R,8S)-8-[(1R)-1-hydroxy-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

: 359887-05-1
(1R,6R,8S)-8-[(1R)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

: 359887-06-2
(1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

Guidance literature:: With dmap; triethylamine; WSC*HCl; In dichloromethane;
DOI:10.1016/S0040-4039(01)00817-6

Reference yield:

: 56423-39-3,36747-83-8
trans-4-methylpent-2-enal

: 359887-06-2
(1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

Guidance literature:: Multi-step reaction with 9 steps

1.1: i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 - -18 °C

1.2: 50 percent / pyridine / 2.5 h / 0 °C

2.1: CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / -78 - -18 °C

2.2: imidazole / dimethylformamide / 2 h / 0 °C

2.3: 1.51 g / diisobutylaluminium hydride / CH₂Cl₂; toluene / 1.5 h / -78 °C

3.1: 78 percent / VO(acac)2; t-BuOOH / CH₂Cl₂; toluene / 2.5 h / 0 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

5.1: 1.34 g / tetrahydrofuran; diethyl ether / 1 h / 0 °C

6.1: 93 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 1.5 h / 0 °C

7.1: 98 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 0 °C

8.1: 98 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / -18 °C

9.1: 47 percent / WSC*HCl; Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

With tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; bis(acetylacetonate)oxovanadium; WSC*HCl; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 4.1: Dess-Martin oxidation;
DOI:10.1021/jo0203140

Reference yield:

: rel-(3R,4R)-4-[(1S,2E)-1-hydroxy-5-methyl-2-hexenyl]-1-methyl-3-triethylsilyloxy-1-cyclohexene

: 359887-06-2
(1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / VO(acac)2; t-BuOOH / CH₂Cl₂; toluene / 2.5 h / 0 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

3: 1.34 g / tetrahydrofuran; diethyl ether / 1 h / 0 °C

4: 93 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 1.5 h / 0 °C

5: 98 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 0 °C

6: 98 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / -18 °C

7: 47 percent / WSC*HCl; Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

With tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; WSC*HCl; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2: Dess-Martin oxidation;
DOI:10.1021/jo0203140