p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate

Base Information

• Chemical Name: p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate
• CAS No.: 91273-91-5
• Molecular Formula: C₂₀H₂₈O₇S
• Molecular Weight: 412.504
• Mol file: 91273-91-5.mol

Synonyms:p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate

Chemical Property of p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate

There total 11 articles about p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate 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: 75.0%

2-(p-tolylsulfonyl)ethyl (2E,4R,5R,7R)-4,5,7-trihydroxy-2-octenoate (91273-90-4) + acetone (67-64-1) → p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate (91273-91-5)

Guidance literature:

With toluene-4-sulfonic acid; 2,2-dimethoxy-propane; for 60h; Ambient temperature;

DOI:10.1016/S0040-4039(01)81187-4

Reference yield:

methyl 4,6-dideoxy-α-D-arabino-hexopyranoside (55338-33-5) → p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate (91273-91-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Dowex-50W(H⁺) / H₂O / 8.5 h / Heating

2: benzene / 18 h / Heating

3: p-tolenesulfonic acid, acetone / 64 h / Ambient temperature

With Dowex-50W(H⁺); toluene-4-sulfonic acid; acetone; In water; benzene;

DOI:10.1246/bcsj.66.523

Reference yield:

D-arabino-4,6-dideoxy-hexose (22435-60-5,23583-37-1,29325-32-4,33302-99-7,66900-21-8,116907-46-1,116907-47-2,132957-12-1,132957-13-2,1279230-33-9) → p-toluenesulfonylethyl (4R,5R,7R,2E)-7-hydroxy-4,5-dimethylmethylenedioxy-2-octenoate (91273-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / 18 h / Heating

2: p-tolenesulfonic acid, acetone / 64 h / Ambient temperature

With toluene-4-sulfonic acid; acetone; In benzene;

DOI:10.1246/bcsj.66.523

upstream raw materials:

(E)-(4S,5S,7R)-4,5,7-Trihydroxy-oct-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

2,2-dimethoxy-propane

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

D-xylo-4,6-dideoxy-hexose

Downstream raw materials:

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

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

(E)-(S)-5-(Tetrahydro-pyran-2-yloxy)-hex-2-enoic acid (R)-2-((4R,5R)-2,2-dimethyl-5-{(E)-2-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-vinyl}-[1,3]dioxolan-4-yl)-1-methyl-ethyl ester

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