(2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane

Base Information

Chemical Name:(2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane
CAS No.:1412945-18-6
Molecular Formula:C₁₈H₃₀O₅SSi
Molecular Weight:386.585
Hs Code.:

Synonyms:(2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane

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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 (2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane

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Technology Process of (2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane

There total 5 articles about (2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane 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%

: 1412945-20-0
2-{(2S,3S)-3-[(tert-butyldimethylsiloxy)methyl]oxiran-2-yl}ethanol

: 98-59-9
p-toluenesulfonyl chloride

: 1412945-18-6
(2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1055/s-0032-1316734

Reference yield:

: 146916-76-9
5-(4-methoxyphenyl)methoxy-2-pentyn-1-ol

: 1412945-18-6
(2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane

Guidance literature:: Multi-step reaction with 5 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; tert.-butylhydroperoxide / dichloromethane; toluene / -20 °C / Inert atmosphere; Molecular sieve

3: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

5: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene; 2: |Sharpless Asymmetric Epoxidation;
DOI:10.1055/s-0032-1316734

Reference yield:

: 1412945-17-5
(2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-methoxybenzyloxy)ethyl]oxirane

: 1412945-18-6
(2S,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane

Guidance literature:: Multi-step reaction with 2 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1055/s-0032-1316734