(2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate

Base Information

Chemical Name:(2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate
CAS No.:1426540-32-0
Molecular Formula:C₂₆H₄₂O₅Si
Molecular Weight:462.702
Hs Code.:

Synonyms:(2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate

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Chemical Property of (2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate

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Technology Process of (2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate

There total 4 articles about (2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate 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: 94.0%

: 1426540-31-9
(2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-(hydroxymethyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1426540-32-0
(2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 2.16667h;
DOI:10.1021/jo400001t

Reference yield:

: 1426540-19-3
(2S,3R,4E)-3-(2-(benzyloxy)ethyl)-6-(4-methoxybenzyloxy)-2-(prop-1-en-2-yl)hex-4-en-1-ol

: 1426540-32-0
(2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine; dmap / dichloromethane / 5 h / 0 - 20 °C

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

3: titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N-diethyltryptamine / dichloromethane / 5 h / -20 °C / Molecular sieve

4: 1H-imidazole / dichloromethane / 2.17 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; N,N-diethyltryptamine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1021/jo400001t

Reference yield:

: 1426540-28-4
methyl (2S,3R,4E)-3-(2-(benzyloxy)ethyl)-6-(4-methoxybenzyloxy)-2-(prop-1-en-2-yl)hex-4-enoate

: 1426540-32-0
(2S,3S)-5-(benzyloxy)-3-((2R,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-2-(prop-1-en-2-yl)pentyl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C

2: triethylamine; dmap / dichloromethane / 5 h / 0 - 20 °C

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

4: titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N-diethyltryptamine / dichloromethane / 5 h / -20 °C / Molecular sieve

5: 1H-imidazole / dichloromethane / 2.17 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; N,N-diethyltryptamine; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1021/jo400001t