Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ⁶-thia-bicyclo[4.2.0]oct-4-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ⁶-thia-bicyclo[4.2.0]oct-4-yl ester
• CAS No.: 101155-80-0
• Molecular Formula: C₁₄H₁₈O₈S₂
• Molecular Weight: 378.424

Synonyms:Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ⁶-thia-bicyclo[4.2.0]oct-4-yl ester

Chemical Property of Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ⁶-thia-bicyclo[4.2.0]oct-4-yl ester

Chemical Property:

Purity/Quality:

99% ，98% ^*data from raw suppliers

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• Pictogram(s):  
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Technology Process of Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ⁶-thia-bicyclo[4.2.0]oct-4-yl ester

There total 5 articles about Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ⁶-thia-bicyclo[4.2.0]oct-4-yl 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: 80.0%

methyl 2-O-p-toluenesulfonyl-4,6-thioanhydro-α-D-gulopyranoside (101155-78-6) → Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ6-thia-bicyclo[4.2.0]oct-4-yl ester (101155-80-0)

Guidance literature:

With monoperoxyphthalic acid; In diethyl ether; for 5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96374-4

Reference yield:

methyl 4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside (10368-81-7) → Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ6-thia-bicyclo[4.2.0]oct-4-yl ester (101155-80-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 94.59 percent / pyridine / 240 h / Ambient temperature

2: 68.1 percent / butan-2-one / 0.5 h / Heating

3: 84 percent / benzene; methanol / 3 h / Ambient temperature

4: 80 percent / 0.16 M monoperphthalic acid / diethyl ether / 5 h / Ambient temperature

With monoperoxyphthalic acid; In pyridine; methanol; diethyl ether; butanone; benzene;

DOI:10.1016/S0040-4020(01)96374-4

Reference yield:

methyl 2,3-di-O-p-toluenesulfonyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside (101155-76-4) → Toluene-4-sulfonic acid (1R,3S,4R,5S,6R)-5-hydroxy-3-methoxy-7,7-dioxo-2-oxa-7λ6-thia-bicyclo[4.2.0]oct-4-yl ester (101155-80-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 68.1 percent / butan-2-one / 0.5 h / Heating

2: 84 percent / benzene; methanol / 3 h / Ambient temperature

3: 80 percent / 0.16 M monoperphthalic acid / diethyl ether / 5 h / Ambient temperature

With monoperoxyphthalic acid; In methanol; diethyl ether; butanone; benzene;

DOI:10.1016/S0040-4020(01)96374-4

upstream raw materials:

methyl 2-O-p-toluenesulfonyl-4,6-thioanhydro-α-D-gulopyranoside

methyl 4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside

methyl 2,3-di-O-p-toluenesulfonyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside

methyl 2,3-di-O-p-toluenesulfonyl-4-O-benzoyl-6-S-acetyl-6-thio-α-D-glucopyranoside

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