(4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl ester

Base Information

• Chemical Name: (4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl ester
• CAS No.: 922736-45-6
• Molecular Formula: C₃₅H₃₈O₆
• Molecular Weight: 554.683
• Mol file: 922736-45-6.mol

Synonyms:(4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl ester

Chemical Property of (4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl ester

There total 1 articles about (4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl 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: 91.0%

propynoic acid methyl ester (922-67-8) + (6R,7S,8R)-6,7,8-Tris-benzyloxy-deca-1,9-dien-5-one (347897-59-0) → (4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl ester (922736-45-6)

Guidance literature:

propynoic acid methyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0166667h;

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 ℃; for 0.666667h;

(6R,7S,8R)-6,7,8-Tris-benzyloxy-deca-1,9-dien-5-one; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1016/j.jorganchem.2006.07.014

Reference yield: 74.0%

(4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl ester (922736-45-6) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-triethylsilanyloxy-non-8-en-2-ynoic acid methyl ester (920266-26-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.jorganchem.2006.07.014

Reference yield:

(4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-hydroxy-non-8-en-2-ynoic acid methyl ester (922736-45-6) → 2-[(R)-5-Triethylsilanyloxy-5-((1R,2S,3R)-1,2,3-tris-benzyloxy-pent-4-enyl)-cyclopent-1-enyl]-acrylic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

2: 42 percent / Ru-catalyst / CH₂Cl₂ / 18 h / Heating

With 2,6-dimethylpyridine; Ru-catalyst; In dichloromethane;

DOI:10.1016/j.jorganchem.2006.07.014

upstream raw materials:

propynoic acid methyl ester

(6R,7S,8R)-6,7,8-Tris-benzyloxy-deca-1,9-dien-5-one

Downstream raw materials:

(4R,5R,6S,7R)-5,6,7-Tris-benzyloxy-4-but-3-enyl-4-triethylsilanyloxy-non-8-en-2-ynoic acid methyl ester