tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)carbamate

Base Information

• Chemical Name: tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)carbamate
• CAS No.: 1413176-70-1
• Molecular Formula: C₂₇H₄₄N₂O₅Si
• Molecular Weight: 504.742
• Mol file: 1413176-70-1.mol

Synonyms:tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)carbamate

Chemical Property of tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)carbamate

There total 6 articles about tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)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: 51.5%

C21H34N2O3Si + 2,2-dimethylpropanoic anhydride (1538-75-6) → tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)carbamate (1413176-70-1)

Guidance literature:

C₂₁H₃₄N₂O₃Si; With dmap; triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;

2,2-dimethylpropanoic anhydride; In tetrahydrofuran; Inert atmosphere; Reflux;

DOI:10.1039/c2cc35484e

Reference yield:

(S)-1-(tert-butyldimethylsilyloxy)-N-(4-methoxybenzyl)but-3-en-2-amine (1413176-67-6) → tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)carbamate (1413176-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 20 °C / Cooling with ice

2.1: dmap; triethylamine / tetrahydrofuran / 0.5 h / 0 °C

2.2: Inert atmosphere; Reflux

With dmap; triethylamine; In tetrahydrofuran;

DOI:10.1039/c2cc35484e

Reference yield:

methyl (R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzylamino)propanoate (1413176-63-2) → tert-butyl (S)-allyl((1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)(4-methoxybenzyl)carbamoyl)carbamate (1413176-70-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

1.2: 0 °C / Inert atmosphere; Reflux

1.3: -78 °C

2.1: Tabbe’s reagent / tetrahydrofuran; toluene / 2 h / 20 °C

3.1: N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 24 h / 20 °C

4.1: tetrahydrofuran / 20 °C / Cooling with ice

5.1: dmap; triethylamine / tetrahydrofuran / 0.5 h / 0 °C

5.2: Inert atmosphere; Reflux

With dmap; N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/c2cc35484e

upstream raw materials:

2,2-dimethylpropanoic anhydride

methyl (R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzylamino)propanoate

(R)-methyl 3-hydroxy-2-(4-methoxybenzylamino)propanoate

(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(4-methoxybenzyl)carbamate

Downstream raw materials:

(S)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-3-(4-methoxybenzyl)-2-oxo-2,3,4,7-tetrahydro-1H-1,3-diazepine-1-carboxylate