(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 tris-(2-trimethylsilanyl-ethyl) ester

Base Information

• Chemical Name: (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 tris-(2-trimethylsilanyl-ethyl) ester
• CAS No.: 145294-70-8
• Molecular Formula: C₅₀H₈₂O₁₄Si₃
• Molecular Weight: 991.449
• Mol file: 145294-70-8.mol

Synonyms:(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 tris-(2-trimethylsilanyl-ethyl) ester

Chemical Property of (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 tris-(2-trimethylsilanyl-ethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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 tris-(2-trimethylsilanyl-ethyl) ester

There total 1 articles about (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 tris-(2-trimethylsilanyl-ethyl) 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: 83.0%

zaragozic acid A (138682-84-5,144786-97-0,146075-86-7,148152-80-1,149656-40-6,142561-96-4) + O-<2-(trimethylsilyl)ethyl>-N,N'-diisopropylisourea → (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 tris-(2-trimethylsilanyl-ethyl) ester (145294-70-8)

Guidance literature:

In benzene; at 65 ℃; for 16h;

DOI:10.1021/jo00052a032

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 tris-(2-trimethylsilanyl-ethyl) ester (145294-70-8) → (1S,3S,4S,5R,6R,7R)-4,6-Dihydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(2-trimethylsilanyl-ethoxymethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tris-(2-trimethylsilanyl-ethyl) ester

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / N,N'-diisopropylethylamine / CH₂Cl₂ / 24 h / Heating

2: 66 percent / Ti(OEt)4, 2-(trimethylsilyl)ethanol / 24 h / 100 °C

With titanium(IV) tetraethanolate; 2-(Trimethylsilyl)ethanol; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00052a032

upstream raw materials:

zaragozic acid A