(R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

Base Information

Chemical Name:(R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine
CAS No.:1241959-25-0
Molecular Formula:C₃₂H₄₁NO₂Si
Molecular Weight:499.769
Hs Code.:

Synonyms:(R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

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Chemical Property of (R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

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Technology Process of (R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

There total 4 articles about (R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine 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%

: 97682-96-7,99726-01-9,127505-65-1
(2S)-1-(phenylmethoxy)but-3-en-2-ylamine

: (2R,3E)-2-[(t-butyldiphenylsilyl)oxy]pent-3-ene nitrile

: 1241959-25-0
(R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

Guidance literature:: (2R,3E)-2-[(t-butyldiphenylsilyl)oxy]pent-3-ene nitrile; With diisobutylaluminium hydride; In diethyl ether; at -78 - 10 ℃; Inert atmosphere;

(2S)-1-(phenylmethoxy)but-3-en-2-ylamine; In methanol; diethyl ether; at -90 - 20 ℃; Inert atmosphere;

With sodium tetrahydroborate; In methanol; diethyl ether; at 20 ℃; Inert atmosphere; Cooling with ice;
DOI:10.1021/ol101556k

Reference yield:

: 6812-26-6,10017-08-0,116908-78-2,118710-58-0,124439-85-6
(R)-(-)-2-hydroxy-3-(E)-pentenenitrile

: 1241959-25-0
(R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / diethyl ether / -80 - 0 °C / Inert atmosphere

2.2: -90 °C / Inert atmosphere

3.1: sodium tetrahydroborate / 20 h / 20 °C / Inert atmosphere

3.2: -90 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; diisobutylaluminium hydride; In diethyl ether; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201200377

Reference yield:

: (2R,3E)-2-[(t-butyldiphenylsilyl)oxy]pent-3-ene nitrile

: 1241959-25-0
(R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / diethyl ether / -80 - 0 °C / Inert atmosphere

1.2: -90 °C / Inert atmosphere

2.1: sodium tetrahydroborate / 20 h / 20 °C / Inert atmosphere

2.2: -90 °C / Inert atmosphere

With sodium tetrahydroborate; diisobutylaluminium hydride; In diethyl ether;
DOI:10.1002/ejoc.201200377