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

Base Information

• Chemical Name: 2-(p-tolylsulfonyl)ethyl (10E,4R,5R,7R,13S)-13-t-butyldimethylsiloxy-4,5-isopropylidenedioxy-7-methyl-9-oxo-8-oxa-10-tetradecenoate
• CAS No.: 133522-15-3
• Molecular Formula: C₃₂H₅₂O₉SSi
• Molecular Weight: 640.911
• Mol file: 133522-15-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

methyl 4,6-dideoxy-α-D-arabino-hexopyranoside (55338-33-5) → 2-(p-tolylsulfonyl)ethyl (10E,4R,5R,7R,13S)-13-t-butyldimethylsiloxy-4,5-isopropylidenedioxy-7-methyl-9-oxo-8-oxa-10-tetradecenoate (133522-15-3)

Guidance literature:

Multi-step reaction with 5 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

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

5: 4-dimethylaminopyridine (DMAP) / toluene / 22 h / Ambient temperature

With dmap; Dowex-50W(H⁺); hydrogen; toluene-4-sulfonic acid; acetone; palladium on activated charcoal; In tetrahydrofuran; water; toluene; 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) → 2-(p-tolylsulfonyl)ethyl (10E,4R,5R,7R,13S)-13-t-butyldimethylsiloxy-4,5-isopropylidenedioxy-7-methyl-9-oxo-8-oxa-10-tetradecenoate (133522-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1: benzene / 18 h / Heating

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

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

4: 4-dimethylaminopyridine (DMAP) / toluene / 22 h / Ambient temperature

With dmap; hydrogen; toluene-4-sulfonic acid; acetone; palladium on activated charcoal; In tetrahydrofuran; toluene; benzene;

DOI:10.1246/bcsj.66.523

Reference yield:

2-(p-tolylsulfonyl)ethyl (2E,4R,5R,7R)-4,5,7-trihydroxy-2-octenoate (91273-90-4) → 2-(p-tolylsulfonyl)ethyl (10E,4R,5R,7R,13S)-13-t-butyldimethylsiloxy-4,5-isopropylidenedioxy-7-methyl-9-oxo-8-oxa-10-tetradecenoate (133522-15-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 100 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 3 h / 14710.2 Torr / Ambient temperature

3: 4-dimethylaminopyridine (DMAP) / toluene / 22 h / Ambient temperature

With dmap; hydrogen; toluene-4-sulfonic acid; acetone; palladium on activated charcoal; In tetrahydrofuran; toluene;

DOI:10.1246/bcsj.66.523

upstream raw materials:

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

methyl 4,6-dideoxy-α-D-arabino-hexopyranoside

D-arabino-4,6-dideoxy-hexose

(+)-(S)-t-butyl-3-(t-butyldimethylsilyloxy)-butyrate