(1R,2S,6R,8S,9R,10R)-8-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-10-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-2,9-dihydroxy-3-oxo-4,7,11-trioxa-tricyclo[6.2.1.0^2,6]undecane-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1R,2S,6R,8S,9R,10R)-8-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-10-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-2,9-dihydroxy-3-oxo-4,7,11-trioxa-tricyclo[6.2.1.0^2,6]undecane-1-carboxylic acid tert-butyl ester
• CAS No.: 186097-00-7
• Molecular Formula: C₃₉H₅₄O₁₂
• Molecular Weight: 714.851
• Mol file: 186097-00-7.mol

Synonyms:

Chemical Property of (1R,2S,6R,8S,9R,10R)-8-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-10-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-2,9-dihydroxy-3-oxo-4,7,11-trioxa-tricyclo[6.2.1.0^2,6]undecane-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6R,8S,9R,10R)-8-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-10-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-2,9-dihydroxy-3-oxo-4,7,11-trioxa-tricyclo[6.2.1.0^2,6]undecane-1-carboxylic acid tert-butyl ester

There total 4 articles about (1R,2S,6R,8S,9R,10R)-8-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-10-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-2,9-dihydroxy-3-oxo-4,7,11-trioxa-tricyclo[6.2.1.0^2,6]undecane-1-carboxylic acid tert-butyl 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:

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3-methyl ester → (1R,2S,6R,8S,9R,10R)-8-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-10-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-2,9-dihydroxy-3-oxo-4,7,11-trioxa-tricyclo[6.2.1.02,6]undecane-1-carboxylic acid tert-butyl ester (186097-00-7)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene / Heating

2: aq. NaOH / tetrahydrofuran / Ambient temperature

3: 60 percent / N-hydroxysuccinimide, 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulphonate, NaBH₄ / tetrahydrofuran

4: HCl / dioxane

5: 49 percent / 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulphonate, N-hydroxysuccinimide / tetrahydrofuran / 23 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; In tetrahydrofuran; 1,4-dioxane; toluene;

DOI:10.1016/S0040-4039(96)02049-7

Reference yield:

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4,5-di-tert-butyl ester 3-methyl ester (144571-48-2) → (1R,2S,6R,8S,9R,10R)-8-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-10-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-2,9-dihydroxy-3-oxo-4,7,11-trioxa-tricyclo[6.2.1.02,6]undecane-1-carboxylic acid tert-butyl ester (186097-00-7)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NaOH / tetrahydrofuran / Ambient temperature

2: 60 percent / N-hydroxysuccinimide, 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulphonate, NaBH₄ / tetrahydrofuran

3: HCl / dioxane

4: 49 percent / 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulphonate, N-hydroxysuccinimide / tetrahydrofuran / 23 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0040-4039(96)02049-7

Reference yield:

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid di-tert-butyl ester (160905-22-6) → (1R,2S,6R,8S,9R,10R)-8-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-10-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-2,9-dihydroxy-3-oxo-4,7,11-trioxa-tricyclo[6.2.1.02,6]undecane-1-carboxylic acid tert-butyl ester (186097-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane

2: 49 percent / 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluenesulphonate, N-hydroxysuccinimide / tetrahydrofuran / 23 h / Ambient temperature

With hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0040-4039(96)02049-7

upstream raw materials:

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4,5-di-tert-butyl ester 3-methyl ester

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid di-tert-butyl ester

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4,5-di-tert-butyl ester

Downstream raw materials:

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4-carbamoyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4-carbamoyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid tert-butyl ester