(Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid ethyl ester

Base Information

• Chemical Name: (Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid ethyl ester
• CAS No.: 140367-91-5
• Molecular Formula: C₂₅H₃₂O₇S
• Molecular Weight: 476.591
• Mol file: 140367-91-5.mol

Synonyms:(Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid ethyl ester

Chemical Property of (Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid ethyl ester

There total 3 articles about (Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid 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: 95.0%

(Z)-(S)-6-Benzyloxymethoxy-8-hydroxy-oct-4-enoic acid ethyl ester (140367-90-4) + p-toluenesulfonyl chloride (98-59-9) → (Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid ethyl ester (140367-91-5)

Guidance literature:

With triethylamine; dmap; In dichloromethane;

DOI:10.1016/0040-4039(91)80195-C

Reference yield:

(S)-2-Benzyloxymethoxy-4-hydroxy-butyraldehyde (163041-37-0) → (Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid ethyl ester (140367-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hexamethylsilazane / -78 - 0 °C

2: triethylamine / dmap / dichloromethane

With potassium hexamethylsilazane; triethylamine; dmap; In dichloromethane;

DOI:10.1016/0040-4039(91)80195-C

Reference yield:

(S)-3-hydroxybutyrolactone, benzyloxy methyl ether (73991-96-5) → (Z)-(S)-6-Benzyloxymethoxy-8-(toluene-4-sulfonyloxy)-oct-4-enoic acid ethyl ester (140367-91-5)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / tetrahydrofuran / -78 °C

2: potassium hexamethylsilazane / -78 - 0 °C

3: triethylamine / dmap / dichloromethane

With potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; dmap; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(91)80195-C

upstream raw materials:

(Z)-(S)-6-Benzyloxymethoxy-8-hydroxy-oct-4-enoic acid ethyl ester

p-toluenesulfonyl chloride

(S)-3-hydroxybutyrolactone, benzyloxy methyl ether

(S)-2-Benzyloxymethoxy-4-hydroxy-butyraldehyde

Downstream raw materials:

4-((S)-3-Benzyloxymethoxy-4,5-dihydro-3H-pyrrol-2-yl)-butyric acid ethyl ester

(Z)-(S)-8-Azido-6-benzyloxymethoxy-oct-4-enoic acid

(1S,8aS)-1-Benzyloxymethoxy-1,2,3,5,6,8a-hexahydro-indolizine

(1S,8aS)-1-Benzyloxymethoxy-hexahydro-indolizin-5-one