6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

Base Information

• Chemical Name: 6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester
• CAS No.: 107449-44-5
• Molecular Formula: C₄₁H₅₈O₇
• Molecular Weight: 662.907
• Mol file: 107449-44-5.mol

Synonyms:6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

Chemical Property of 6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

There total 1 articles about 6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl 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: 82.0%

lasalocid benzyl ester (41733-86-2) → 6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester (107449-44-5)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 65 ℃; for 15h;

DOI:10.1016/S0040-4039(00)84628-6

Reference yield:

6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester (107449-44-5) → 6-{(E)-(3R,6S,7S)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-6-hydroxy-3,5-dimethyl-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester (107449-45-6) + 6-{(E)-(3R,6R,7S)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-6-hydroxy-3,5-dimethyl-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester (107494-41-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -5 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)84628-6

Reference yield:

6-{(E)-(3R,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-oxo-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester (107449-44-5) → 6-[(R)-3-((2R,3S)-3-{(R)-2-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-butyryl}-3-methyl-oxiranyl)-butyl]-2-hydroxy-3-methyl-benzoic acid benzyl ester (107449-47-8,107494-43-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / methanol / -5 °C

2: VO(acac)2, t-BuOOH

3: Jones oxidation

With tert.-butylhydroperoxide; sodium tetrahydroborate; bis(acetylacetonate)oxovanadium; In methanol;

DOI:10.1016/S0040-4039(00)84628-6

upstream raw materials:

lasalocid benzyl ester

Downstream raw materials:

6-{(E)-(3R,6S,7S)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-6-hydroxy-3,5-dimethyl-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

6-{(E)-(3R,6R,7S)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-6-hydroxy-3,5-dimethyl-non-4-enyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

6-[(R)-3-((2R,3S)-3-{(R)-2-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-butyryl}-3-methyl-oxiranyl)-butyl]-2-hydroxy-3-methyl-benzoic acid benzyl ester

6-[(R)-3-((2S,3R)-3-{(R)-2-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-butyryl}-3-methyl-oxiranyl)-butyl]-2-hydroxy-3-methyl-benzoic acid benzyl ester