1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene

Base Information

Chemical Name:1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene
CAS No.:248271-10-5
Molecular Formula:C₂₇H₃₈O₇SSi
Molecular Weight:534.746
Hs Code.:

Synonyms:1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene

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Chemical Property of 1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene

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Technology Process of 1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene

There total 5 articles about 1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene 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:

: 98-59-9
p-toluenesulfonyl chloride

: 248271-44-5
1-[(2R)-2,3-dihydroxypropoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene

: 248271-10-5
1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene

Guidance literature:: With dibutyldimethoxytin; triethylamine; In toluene; at 20 ℃; for 17h;
DOI:10.1021/jo990772h

Reference yield:

: 1777-03-3
2-triethylsilylacetylene

: 248271-10-5
1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 3 h / -78 °C

2: p-TsOH*H₂O / methanol / 12 h / 20 °C

3: Bu₂Sn(OMe)2; Et₃N / toluene / 17 h / 20 °C

With n-butyllithium; boron trifluoride diethyl etherate; dibutyldimethoxytin; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; hexane; toluene; 1: Addition / 2: Hydrolysis / 3: Substitution;
DOI:10.1021/jo990772h

Reference yield:

: 248270-73-7
1-[(2R)-2,3-dihydroxy-2,3-isopropylidenepropoxy]-2-hydroxybenzene

: 248271-10-5
1-[(2S)-2,3-dihydroxy-3-(p-toluenesulfonyl)propoxy]-2-[(2S)-2-hydroxy-5-(triethylsilyl)pent-4-ynoxy]benzene

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 72 h / 20 °C

2: 78 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 3 h / -78 °C

3: p-TsOH*H₂O / methanol / 12 h / 20 °C

4: Bu₂Sn(OMe)2; Et₃N / toluene / 17 h / 20 °C

With n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; dibutyldimethoxytin; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Addition / 3: Hydrolysis / 4: Substitution;
DOI:10.1021/jo990772h