2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene

Base Information

Chemical Name:2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene
CAS No.:300810-65-5
Molecular Formula:C₃₈H₅₀O₁₀SSi
Molecular Weight:726.961
Hs Code.:

Synonyms:2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene

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Chemical Property of 2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene

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Technology Process of 2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene

There total 5 articles about 2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene 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:

: 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

: 300810-65-5
2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene

Guidance literature:: Multi-step reaction with 5 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

With pyridine; methyllithium; diisobutylaluminium hydride; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Reduction / 2.1: silylation / 3.1: Metallation / 3.2: Alkylation / 4.1: desilylation / 5.1: Acetylation;
DOI:10.1021/ja000519v

Reference yield:

: (2S,3R,4R,5S,6S)-2-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-iodo-5,6-dimethoxy-3-methyl-phenoxy]-4-methoxy-6-methyl-tetrahydro-pyran-3,5-diol

: 300810-65-5
2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

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

2.2: 74 percent / diethyl ether / 0.17 h / -78 °C

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

4.1: pyridine / 3 h / 25 °C

With pyridine; methyllithium; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: silylation / 2.1: Metallation / 2.2: Alkylation / 3.1: desilylation / 4.1: Acetylation;
DOI:10.1021/ja000519v

Reference yield:

: 300810-64-4
2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthio-toluene

: 300810-65-5
2-((tert-butyldiphenylsiloxy)methyl)-5-((6-deoxy-2,4-di-O-acetyl-3-O-methyl-α-L-mannopyranosyl)oxy)-3,4-dimethoxy-6-methylthiotoluene

Guidance literature:: Multi-step reaction with 2 steps

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

2: pyridine / 3 h / 25 °C

With pyridine; acetic acid; In tetrahydrofuran; 1: desilylation / 2: Acetylation;
DOI:10.1021/ja000519v