(E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene

Base Information

Chemical Name:(E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene
CAS No.:341544-06-7
Molecular Formula:C₃₃H₅₇NO₃Si
Molecular Weight:543.906
Hs Code.:

Synonyms:(E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene

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Chemical Property of (E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene

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Technology Process of (E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene

There total 1 articles about (E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene 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: 83.0%

: 184047-86-7
Benzyl-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-prop-(E)-ylidene]-amine

: acrolein (S,S)-1,2-dicyclohexylethylene acetal

: 341544-06-7
(E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene

Guidance literature:: acrolein (S,S)-1,2-dicyclohexylethylene acetal; With titanium(IV) isopropylate; isopropylmagnesium chloride; In diethyl ether; at -50 - -40 ℃; for 1.5h;

Benzyl-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-prop-(E)-ylidene]-amine; In diethyl ether; at -40 - 20 ℃; for 4h; Further stages.;
DOI:10.1021/ja004140k

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 341544-06-7
(E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene

: Benzyl-[(E)-(R)-1-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((1S,2S)-1,2-dicyclohexyl-2-hydroxy-ethoxy)-but-3-enyl]-carbamic acid tert-butyl ester

Guidance literature:: With triethylamine; In tetrahydrofuran; at 50 ℃; for 12h;
DOI:10.1021/ja004140k

Reference yield:

: 341544-06-7
(E)-(4R,5S)-5-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1S,2S)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-hexene

: 3-(benzyl-tert-butoxycarbonyl-amino)-4-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N / tetrahydrofuran / 12 h / 50 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: dimethyl sulfide / CH₂Cl₂ / 12 h / -78 - 20 °C

3.1: NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; ozone; triethylamine; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja004140k