2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate

Base Information

• Chemical Name: 2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate
• CAS No.: 133463-55-5
• Molecular Formula: C₂₀H₃₀O₇S
• Molecular Weight: 414.52
• Mol file: 133463-55-5.mol

Synonyms:2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate

Chemical Property of 2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate

There total 6 articles about 2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate 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: 100.0%

2-(p-tolylsulfonyl)ethyl (2E,4S,5S,7R)-7-hydroxy-4,5-isopropylidenedioxy-2-octenoate (148406-82-0) → 2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate (133463-55-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 3h; under 14710.2 Torr; Ambient temperature;

DOI:10.1246/bcsj.66.523

Reference yield:

(E)-3-[(4S,5S)-5-((R)-2-Hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid 2-(toluene-4-sulfonyl)-ethyl ester (91273-91-5,148406-82-0) → 2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate (133463-55-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 3h; under 14710.2 Torr; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)79484-6

Reference yield:

methyl 4,6-dideoxy-α-D-glucopyranoside (20585-18-6) → 2-(p-Toluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-(4,5-dimethylmethylene)dioxyoctanoate (133463-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / Dowex-50W(H⁺) / H₂O / 8.5 h / Heating

2: benzene / 21.5 h / Heating

3: p-toluenesulfonic acid, acetone / 77 h / Ambient temperature

4: 100 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 3 h / 14710.2 Torr / Ambient temperature

With Dowex-50W(H⁺); hydrogen; toluene-4-sulfonic acid; acetone; palladium on activated charcoal; In tetrahydrofuran; water; benzene;

DOI:10.1246/bcsj.66.523

upstream raw materials:

(E)-3-[(4S,5S)-5-((R)-2-Hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid 2-(toluene-4-sulfonyl)-ethyl ester

2-(p-tolylsulfonyl)ethyl (2E,4S,5S,7R)-7-hydroxy-4,5-isopropylidenedioxy-2-octenoate

methyl 4,6-dideoxy-α-D-glucopyranoside

D-xylo-4,6-dideoxy-hexose

Downstream raw materials:

2-(p-tolylsulfonyl)ethyl (10E,4S,5S,7R,13S)-13-t-butyldimethylsiloxy-4,5-isopropylidenedioxy-7-methyl-9-oxo-8-oxa-10-tetradecenoate

2-(p-tolylsulfonyl)ethyl (10E,4S,5S,7R,13R)-13-t-butyldimethylsiloxy-4,5-isopropylidenedioxy-7-methyl-9-oxo-8-oxa-10-tetradecenoate