rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol

Base Information

Chemical Name:rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol
CAS No.:100572-45-0
Molecular Formula:C₁₉H₃₂O₂SSi
Molecular Weight:352.613
Hs Code.:

Synonyms:rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol

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Technology Process of rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol

There total 4 articles about rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol 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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 100572-44-9
rel-(2R,3R)-3-isopropenyl-4-(phenylthio)-1,2-butanediol

: 100572-45-0
rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 18h;
DOI:10.1021/jo00356a021

Reference yield:

: 100229-51-4,100758-70-1
(S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-but-3-en-1-ol

: 100572-45-0
rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / n-Bu₃P / tetrahydrofuran / 18 h / 0 - 25 °C

2: 89 percent / Bio-Rad 50W-X₈ cation exchange resin / methanol / 18 h / 25 °C

3: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 18 h / 0 - 25 °C

With dmap; tributylphosphine; Bio-Rad 50W-X₈ cation exchange resin; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00356a021

Reference yield:

: 100572-42-7
rel-(5R,6S)-2,2-dimethyl-5-hydroxy-6-isopropenyl-1,3-dioxepane

: 100572-45-0
rel-(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-isopropenyl-4-(phenylthio)-2-butanol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / p-TsOH / acetone / 25 °C

2: 87 percent / n-Bu₃P / tetrahydrofuran / 18 h / 0 - 25 °C

3: 89 percent / Bio-Rad 50W-X₈ cation exchange resin / methanol / 18 h / 25 °C

4: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 18 h / 0 - 25 °C

With dmap; tributylphosphine; Bio-Rad 50W-X₈ cation exchange resin; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1021/jo00356a021