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

Base Information

• Chemical Name: (R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine
• CAS No.: 1241959-30-7
• Molecular Formula: C₃₂H₄₁NO₂Si
• Molecular Weight: 499.769
• Mol file: 1241959-30-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (R,E)-N-((R)-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: 78.0%

(R)-1-(benzyloxy)but-3-en-2-amine (97682-96-7) + (2R,3E)-2-[(t-butyldiphenylsilyl)oxy]pent-3-ene nitrile → (R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine (1241959-30-7)

Guidance literature:

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

(R)-1-(benzyloxy)but-3-en-2-amine; In methanol; diethyl ether; at -90 - 20 ℃; Inert atmosphere;

With sodium tetrahydroborate; In methanol; diethyl ether; at 20 ℃; Cooling with ice; Inert atmosphere;

DOI:10.1021/ol101556k

Reference yield:

(R)-1-(benzyloxy)but-3-en-2-amine (97682-96-7) + C21H26O2Si → (R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine (1241959-30-7)

Guidance literature:

(R)-1-(benzyloxy)but-3-en-2-amine; C₂₁H₂₆O₂Si; With sodium tetrahydroborate; In diethyl ether; for 20h; Inert atmosphere;

With methanol; at -90 ℃; Inert atmosphere;

(R)-1-(benzyloxy)but-3-en-2-amine; With sodium tetrahydroborate; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/ejoc.201200377

Reference yield:

(R)-(-)-2-hydroxy-3-(E)-pentenenitrile (6812-26-6,10017-08-0,116908-78-2,118710-58-0,124439-85-6) → (R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine (1241959-30-7)

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 / diethyl ether / 20 h / 20 0 °C / Inert atmosphere

3.2: -90 °C / Inert atmosphere

3.3: 20 h / 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; diisobutylaluminium hydride; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201200377

upstream raw materials:

(R)-1-(benzyloxy)but-3-en-2-amine

(R)-(-)-2-hydroxy-3-(E)-pentenenitrile

Downstream raw materials:

tert-butyl (R)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate

tert-butyl (3R,6R)-6-((benzyloxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate

(2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

tert-butyl (2S,3S,4R,5S)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate