4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid

Base Information

Chemical Name:4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid
CAS No.:300810-68-8
Molecular Formula:C₂₂H₃₀O₁₁S
Molecular Weight:502.54
Hs Code.:

Synonyms:4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid

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Chemical Property of 4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid

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Technology Process of 4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid

There total 8 articles about 4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid 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: 74.0%

: 300810-67-7
4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-4-hydroxymethyl-6-methylthio-toluene

: 300810-68-8
4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid

Guidance literature:: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 1.5h; Heating;
DOI:10.1021/ja000519v

Reference yield:

: 153693-41-5
2-((tert-butyldiphenylsilyloxy)methyl)-5-<(4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-α-L-mannopyranosyl)oxy>-3,4-dimethoxy-6-iodotoluene

: 300810-68-8
4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 72 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / -78 - -20 °C

2.1: 94 percent / Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

3.1: MeLi / diethyl ether / 0.08 h / -78 °C

3.2: 74 percent / diethyl ether / 0.17 h / -78 °C

4.1: aq. AcOH / tetrahydrofuran / 12 h / 25 °C

5.1: pyridine / 3 h / 25 °C

6.1: 88 percent / HF*pyridine / tetrahydrofuran / 3 h

7.1: 88 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1 h / -78 - -40 °C

8.1: 74 percent / NBS; AIBN / CCl₄ / 1.5 h / Heating

With pyridine; N-Bromosuccinimide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); methyllithium; diisobutylaluminium hydride; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; toluene; 1.1: Reduction / 2.1: silylation / 3.1: Metallation / 3.2: Alkylation / 4.1: desilylation / 5.1: Acetylation / 6.1: desilylation / 7.1: Swern oxidation / 8.1: Oxidation;
DOI:10.1021/ja000519v

Reference yield:

: 300810-66-6
5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-4-hydroxymethyl-6-methylthio-toluene

: 300810-68-8
4-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-Lmannopyranosyl)oxy)-2,3-dimethoxy-6-methyl-5-methylthio-benzoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 88 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1 h / -78 - -40 °C

2: 74 percent / NBS; AIBN / CCl₄ / 1.5 h / Heating

With N-Bromosuccinimide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); dimethyl sulfoxide; triethylamine; In tetrachloromethane; dichloromethane; 1: Swern oxidation / 2: Oxidation;
DOI:10.1021/ja000519v