(2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene

Base Information

• Chemical Name: (2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene
• CAS No.: 812646-20-1
• Molecular Formula: C₂₆H₄₀N₂OSi
• Molecular Weight: 424.702
• Mol file: 812646-20-1.mol

Synonyms:(2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene

Chemical Property of (2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene

There total 3 articles about (2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene 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:

(Z)-2-Butene (590-18-1) + O-(tert-butyldimethylsilanyl)hydroxylamine (41879-39-4) + 2-N,N-Dibenzylaminoacetaldehyde (106889-84-3) → (2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene (812646-20-1)

Guidance literature:

(Z)-2-Butene; 2-N,N-Dibenzylaminoacetaldehyde; With n-butyllithium; potassium tert-butylate; (+)-B-methoxydiisocamphenylborane; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 5h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; diethyl ether; hexane; for 1h; Heating;

O-(tert-butyldimethylsilanyl)hydroxylamine; With trifluoromethylsulfonic anhydride; lutidine; In hexane; dichloromethane; at -78 - 24 ℃; for 6.5h;

DOI:10.1021/jo0486387

Reference yield:

N,N-dibenzyl-2-aminoethanol (101-06-4) → (2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene (812646-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N; SO₃*Py / dimethylsulfoxide / 1 h / 24 °C

2.1: n-BuLi; t-BuOK; (+)-(Ipc)2BOMe / BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 5 h / -78 °C

2.2: aq. NaOH; H₂O₂ / tetrahydrofuran; hexane; diethyl ether / 1 h / Heating

2.3: 81 mg / Tf₂O; lutidine / CH₂Cl₂; hexane / 6.5 h / -78 - 24 °C

With n-butyllithium; pyridine-SO₃ complex; potassium tert-butylate; triethylamine; (+)-B-methoxydiisocamphenylborane; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; hexane; dimethyl sulfoxide;

DOI:10.1021/jo0486387

Reference yield:

benzyl bromide (100-39-0) → (2S,3S)-2-dibenzylamino-1-(tert-butyldimethylsilanyloxy)amino-3-methyl-4-pentene (812646-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Na₂CO₃ / CH₂Cl₂; H₂O / 3 h / Heating

2.1: Et₃N; SO₃*Py / dimethylsulfoxide / 1 h / 24 °C

3.1: n-BuLi; t-BuOK; (+)-(Ipc)2BOMe / BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 5 h / -78 °C

3.2: aq. NaOH; H₂O₂ / tetrahydrofuran; hexane; diethyl ether / 1 h / Heating

3.3: 81 mg / Tf₂O; lutidine / CH₂Cl₂; hexane / 6.5 h / -78 - 24 °C

With n-butyllithium; pyridine-SO₃ complex; potassium tert-butylate; sodium carbonate; triethylamine; (+)-B-methoxydiisocamphenylborane; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jo0486387

upstream raw materials:

(Z)-2-Butene

O-(tert-butyldimethylsilanyl)hydroxylamine

2-N,N-Dibenzylaminoacetaldehyde

N,N-dibenzyl-2-aminoethanol

Refernces