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

Base Information

• Chemical Name: tert-butyl (S)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate
• CAS No.: 1241959-28-3
• Molecular Formula: C₃₇H₄₉NO₄Si
• Molecular Weight: 599.886
• Mol file: 1241959-28-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about tert-butyl (S)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + (R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine (1241959-25-0) → tert-butyl (S)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate (1241959-28-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 50 ℃; Inert atmosphere;

DOI:10.1021/ol101556k

Reference yield:

C21H26O2Si → tert-butyl (S)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate (1241959-28-3)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: -90 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran;

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) → tert-butyl (S)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate (1241959-28-3)

Guidance literature:

Multi-step reaction with 4 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

4.1: triethylamine / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere

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

DOI:10.1002/ejoc.201200377

upstream raw materials:

di-tert-butyl dicarbonate

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

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

Downstream raw materials:

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

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

tert-butyl (2S,5S)-5-benzoyloxy-2-(benzyloxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate

tert-butyl (2S,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate