(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-3,4-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid 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-3,4-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid tert-butyl ester
• CAS No.: 186097-03-0
• Molecular Formula: C₃₉H₅₈O₁₂
• Molecular Weight: 718.882
• Mol file: 186097-03-0.mol

Synonyms:

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-3,4-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid 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-3,4-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid tert-butyl ester

There total 4 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-3,4-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-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 → (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-3,4-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid tert-butyl ester (186097-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene / Heating

2: aq. NaOH / tetrahydrofuran / Ambient temperature

3: HCl / dioxane

4: 1.) (COCl)2, DMF; 3.) NaBH₄ / 1.) CH₂Cl₂; 2.) THF, MeCN, 0 deg C to - 30 deg C, 1 h; 3.) DMF, -78 deg C to -20 deg C, 2 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; N,N-dimethyl-formamide; 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) → (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-3,4-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid tert-butyl ester (186097-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaOH / tetrahydrofuran / Ambient temperature

2: HCl / dioxane

3: 1.) (COCl)2, DMF; 3.) NaBH₄ / 1.) CH₂Cl₂; 2.) THF, MeCN, 0 deg C to - 30 deg C, 1 h; 3.) DMF, -78 deg C to -20 deg C, 2 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; 1,4-dioxane;

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 (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-3,4-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid tert-butyl ester (186097-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane

2: 1.) (COCl)2, DMF; 3.) NaBH₄ / 1.) CH₂Cl₂; 2.) THF, MeCN, 0 deg C to - 30 deg C, 1 h; 3.) DMF, -78 deg C to -20 deg C, 2 h

With hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; N,N-dimethyl-formamide; In 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 5-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

(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