(S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

Base Information

Chemical Name:(S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol
CAS No.:1274953-78-4
Molecular Formula:C₁₆H₂₂O₄
Molecular Weight:278.348
Hs Code.:

Synonyms:(S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

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Chemical Property of (S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

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Technology Process of (S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

There total 3 articles about (S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol 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: 69.0%

: 1208329-03-6
(S,E)-8-(4-methoxy-benzyloxy)-octa-1,5-dien-4-ol

: 1274953-78-4
(S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

Guidance literature:: (S,E)-8-(4-methoxy-benzyloxy)-octa-1,5-dien-4-ol; With titanium(IV) isopropylate; (-)-diethyl tartrate; In dichloromethane; at -20 ℃; for 0.75h; Inert atmosphere;

With tert.-butylhydroperoxide; In dichloromethane; at -20 ℃; for 7h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol2003836

Reference yield:

: 671232-57-8
(E)-5-(4-methoxy-benzyloxy)-pent-2-en-1-al

: 1274953-78-4
(S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: diethyl ether / 3 h / -78 °C / Inert atmosphere

1.2: -78 - 23 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; (-)-diethyl tartrate / dichloromethane / 0.75 h / -20 °C / Inert atmosphere

2.2: 7 h / -20 °C / Inert atmosphere

With titanium(IV) isopropylate; (-)-diethyl tartrate; In diethyl ether; dichloromethane; 2.1: Sharpless epoxidation / 2.2: Sharpless epoxidation;
DOI:10.1021/ol2003836

Reference yield:

: 142860-83-1
1-(4-methoxybenzyloxy)-3-butene

: 1274953-78-4
(S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 °C / Inert atmosphere

2.1: diethyl ether / 3 h / -78 °C / Inert atmosphere

2.2: -78 - 23 °C / Inert atmosphere

3.1: titanium(IV) isopropylate; (-)-diethyl tartrate / dichloromethane / 0.75 h / -20 °C / Inert atmosphere

3.2: 7 h / -20 °C / Inert atmosphere

With titanium(IV) isopropylate; Hoveyda-Grubbs catalyst second generation; (-)-diethyl tartrate; In diethyl ether; dichloromethane; 3.1: Sharpless epoxidation / 3.2: Sharpless epoxidation;
DOI:10.1021/ol2003836