(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

Base Information

• Chemical Name: (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
• CAS No.: 160905-22-6
• Molecular Formula: C₄₃H₆₄O₁₃
• Molecular Weight: 788.973
• Mol file: 160905-22-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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: 60.0%

(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 (144571-49-3) → (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)

Guidance literature:

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

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 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 (160905-22-6)

Guidance literature:

Multi-step reaction with 3 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

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

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / tetrahydrofuran / Ambient temperature

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

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

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

(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

Downstream raw materials:

(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 5-tert-butyl ester

(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

(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

(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