(4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone

Base Information

• Chemical Name: (4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone
• CAS No.: 111149-34-9
• Molecular Formula: C₁₆H₁₈O₃
• Molecular Weight: 258.317
• Mol file: 111149-34-9.mol

Synonyms:(4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone

Chemical Property of (4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone

There total 11 articles about (4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone 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: 90.0%

methyl (4R,5S)-(2Z,6E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methylocta-2,6-dienoate (121896-41-1) → (4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone (111149-34-9)

Guidance literature:

With hydrogenchloride; In methanol; for 0.5h; Ambient temperature;

DOI:10.3987/COM-91-S80

Reference yield:

(3R,4S)-(E)-7-benzyloxy-4-methyl-1-trimethylsilylhept-5-en-1-yn-3-ol (111149-31-6) → (4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone (111149-34-9)

Guidance literature:

DOI:10.1039/c39870000555

Reference yield:

(R)-(Z)-1-benzyloxy-2-(3'-trimethylsilylpropargyloxy)-3-pentene (111149-29-2) → (4R,5S)-(2Z,6E)-8-benzyloxy-4-hydroxy-5-methyl-2,6-octadienoic acid lactone (111149-34-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / n-butyl lithium / tetrahydrofuran / -78 °C

With n-butyllithium; In tetrahydrofuran;

DOI:10.1039/c39870000555

upstream raw materials:

(2Z,6E)-(4S,5S)-8-Benzyloxy-4-hydroxy-5-methyl-octa-2,6-dienoic acid

methyl (4R,5S)-(2Z,6E)-8-benzyloxy-4-tert-butyldimethylsilyloxy-5-methylocta-2,6-dienoate

(3R,4S)-(E)-7-benzyloxy-4-methyl-1-trimethylsilylhept-5-en-1-yn-3-ol

(R)-(Z)-1-benzyloxy-2-(3'-trimethylsilylpropargyloxy)-3-pentene

Downstream raw materials:

(E)-(3S,4S,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-en-4-ol

(E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol

(4S,5S)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-4-methyl-tetrahydro-furan-2-ol

Methanesulfonic acid (3S,4R,5R)-5-((E)-(S)-4-benzyloxy-1-methyl-but-2-enyl)-4-methyl-2-oxo-tetrahydro-furan-3-yl ester