4,11,17-Trioxabicyclo[12.2.1]heptadec-6-ene-3,10-dione, 8-hydroxy-2,9,12-trimethyl-5-[(2R)-2-[(phenylmethoxy)methoxy]butyl]-, (1S,2S,5R,6E,8S,9R,12S,14R)-

Base Information

• Chemical Name: 4,11,17-Trioxabicyclo[12.2.1]heptadec-6-ene-3,10-dione, 8-hydroxy-2,9,12-trimethyl-5-[(2R)-2-[(phenylmethoxy)methoxy]butyl]-, (1S,2S,5R,6E,8S,9R,12S,14R)-
• CAS No.: 849482-43-5
• Molecular Formula: C29H42O8
• Molecular Weight: 518.648
• Mol file: 849482-43-5.mol

Synonyms:

Chemical Property of 4,11,17-Trioxabicyclo[12.2.1]heptadec-6-ene-3,10-dione, 8-hydroxy-2,9,12-trimethyl-5-[(2R)-2-[(phenylmethoxy)methoxy]butyl]-, (1S,2S,5R,6E,8S,9R,12S,14R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,11,17-Trioxabicyclo[12.2.1]heptadec-6-ene-3,10-dione, 8-hydroxy-2,9,12-trimethyl-5-[(2R)-2-[(phenylmethoxy)methoxy]butyl]-, (1S,2S,5R,6E,8S,9R,12S,14R)-

There total 21 articles about 4,11,17-Trioxabicyclo[12.2.1]heptadec-6-ene-3,10-dione, 8-hydroxy-2,9,12-trimethyl-5-[(2R)-2-[(phenylmethoxy)methoxy]butyl]-, (1S,2S,5R,6E,8S,9R,12S,14R)- 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: 80.0%

Benzoic acid (E)-(1R,3S,6R,7S,10R,13S,14S)-10-((R)-2-benzyloxymethoxy-butyl)-3,6,13-trimethyl-5,12-dioxo-4,11,17-trioxa-bicyclo[12.2.1]heptadec-8-en-7-yl ester (849482-32-2) → (E)-(1S,2S,5R,8S,9R,12S,14R)-5-((R)-2-Benzyloxymethoxy-butyl)-8-hydroxy-2,9,12-trimethyl-4,11,17-trioxa-bicyclo[12.2.1]heptadec-6-ene-3,10-dione (849482-43-5)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 5h;

DOI:10.1021/ol0500160

Reference yield:

(R)-3-Benzyloxymethoxy-pentanal (849482-38-8) → (E)-(1S,2S,5R,8S,9R,12S,14R)-5-((R)-2-Benzyloxymethoxy-butyl)-8-hydroxy-2,9,12-trimethyl-4,11,17-trioxa-bicyclo[12.2.1]heptadec-6-ene-3,10-dione (849482-43-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 47 percent / tetrahydrofuran / 2 h / 0 °C

2.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

2.2: 98 percent / DMAP / benzene / 2 h / 20 °C

3.1: 92 percent / HCl / methanol / 1 h / 20 °C

4.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

4.2: 92 percent / DMAP / benzene / 5 h / 20 °C

5.1: 48 percent / (N,N'-Mes₂-imidazolidin-2-yl)Ru=CHPh(PCy₃)Cl₂ / CH₂Cl₂ / 12 h / Heating

6.1: 80 percent / K₂CO₃ / methanol / 5 h / 20 °C

With hydrogenchloride; 2,4,6-trichlorobenzoyl chloride; potassium carbonate; triethylamine; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; In tetrahydrofuran; methanol; dichloromethane; 2.1: Yamaguchi esterification;

DOI:10.1021/ol0500160

Reference yield:

(R)-3-Benzyloxymethoxy-pentan-1-ol (849482-20-8) → (E)-(1S,2S,5R,8S,9R,12S,14R)-5-((R)-2-Benzyloxymethoxy-butyl)-8-hydroxy-2,9,12-trimethyl-4,11,17-trioxa-bicyclo[12.2.1]heptadec-6-ene-3,10-dione (849482-43-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 91 percent / DMSO; TEA; SO₃*pyridine / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 47 percent / tetrahydrofuran / 2 h / 0 °C

3.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

3.2: 98 percent / DMAP / benzene / 2 h / 20 °C

4.1: 92 percent / HCl / methanol / 1 h / 20 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

5.2: 92 percent / DMAP / benzene / 5 h / 20 °C

6.1: 48 percent / (N,N'-Mes₂-imidazolidin-2-yl)Ru=CHPh(PCy₃)Cl₂ / CH₂Cl₂ / 12 h / Heating

7.1: 80 percent / K₂CO₃ / methanol / 5 h / 20 °C

With hydrogenchloride; pyridine-SO₃ complex; TEA; 2,4,6-trichlorobenzoyl chloride; potassium carbonate; dimethyl sulfoxide; triethylamine; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; In tetrahydrofuran; methanol; dichloromethane; 3.1: Yamaguchi esterification;

DOI:10.1021/ol0500160

upstream raw materials:

Benzoic acid (E)-(1R,3S,6R,7S,10R,13S,14S)-10-((R)-2-benzyloxymethoxy-butyl)-3,6,13-trimethyl-5,12-dioxo-4,11,17-trioxa-bicyclo[12.2.1]heptadec-8-en-7-yl ester

(R)-3-Benzyloxymethoxy-pentanal

(R)-3-Benzyloxymethoxy-pentan-1-ol

(R)-3-Benzyloxymethoxy-pentanoic acid methyl ester