(Z)-N⁶-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

Base Information

• Chemical Name: (Z)-N⁶-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine
• CAS No.: 1612146-50-5
• Molecular Formula: C₃₃H₅₇N₃O₂SSi₂
• Molecular Weight: 616.071

Synonyms:(Z)-N⁶-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

Chemical Property of (Z)-N⁶-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

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Technology Process of (Z)-N⁶-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

There total 4 articles about (Z)-N⁶-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine 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: 50.0%

(Z)-5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-enal (1612146-49-2) + 2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole (104617-86-9) → (Z)-N6-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (1612146-50-5)

Guidance literature:

(Z)-5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-enal; 2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole; In dichloromethane; for 1h; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In methanol; dichloromethane; at 20 ℃; for 36h; Inert atmosphere;

DOI:10.1016/j.bmc.2016.08.021

Reference yield: 50.0%

→ (Z)-N6-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (1612146-50-5)

Guidance literature:

In dichloromethane; for 1h;

With sodium tris(acetoxy)borohydride; In methanol; dichloromethane; at 20 ℃; for 36h;

Reference yield:

vanillin (121-33-5,8014-42-4) → (Z)-N6-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (1612146-50-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: boron tribromide / dichloromethane / 6 h / -78 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 50 h / -78 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / toluene; hexane / 2 h / -78 °C / Inert atmosphere

5.1: dichloromethane / 1 h / Inert atmosphere

5.2: 36 h / 20 °C / Inert atmosphere

With 1H-imidazole; sodium hexamethyldisilazane; boron tribromide; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: |Wittig Olefination / 3.2: |Wittig Olefination;

DOI:10.1016/j.bmc.2016.08.021

upstream raw materials:

vanillin

3,4-bis(tert-butyldimethylsilanyloxy)benzaldehyde

(Z)-5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-enal

2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole

Downstream raw materials:

(Z)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pent-1-en-1-yl)benzene-1,2-diol

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