(Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol

Base Information

• Chemical Name: (Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol
• CAS No.: 457638-53-8
• Molecular Formula: C₂₄H₃₂O₃Si
• Molecular Weight: 396.602
• Mol file: 457638-53-8.mol

Synonyms:(Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol

Chemical Property of (Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol

There total 2 articles about (Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol 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: 61.0%

1,4-butenediol (6117-80-2) + (Z)-((4-bromobut-2-en-1-yl)oxy)(tert-butyl)diphenylsilane (226546-07-2) → (Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol (457638-53-8)

Guidance literature:

1,4-butenediol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 25 ℃; for 1h; Inert atmosphere;

(Z)-((4-bromobut-2-en-1-yl)oxy)(tert-butyl)diphenylsilane; In tetrahydrofuran; mineral oil; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.3762/bjoc.5.1

Reference yield:

(Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol (87770-83-0) → (Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol (457638-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / N-bromosuccinimide; dimethyl sulfide / CH₂Cl₂ / 0 - 20 °C

2: 60 percent / sodium hydride / tetrahydrofuran / 0 - 20 °C

With N-Bromosuccinimide; dimethylsulfide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0262643

Reference yield: 98.0%

N-(2-nitrophenyl)methanesulfonamide (85150-03-4) + (Z)-4-[(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy]but-2-en-1-ol (457638-53-8) → N-[(Z)-4-{(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy}but-2-enyl]-N-(2-nitrophenyl)methanesulfonamide (457638-55-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/ol0262643

upstream raw materials:

1,4-butenediol

(Z)-((4-bromobut-2-en-1-yl)oxy)(tert-butyl)diphenylsilane

(Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol

Downstream raw materials:

N-[(Z)-4-{(Z)-4-(tert-butyldiphenylsilanyloxy)but-2-enyloxy}but-2-enyl]-N-(2-nitrophenyl)methanesulfonamide

N-[(Z)-4-{(Z)-4-hydroxybut-2-enyloxy}but-2-enyl]-N-(2-nitrophenyl)methanesulfonamide

N-(2-aminophenyl)-N-[(Z)-4-{(Z)-4-phenylsulfanylbut-2-enyloxy}but-2-enyl]methanesulfonamide

N-(2-nitrophenyl)-N-[(Z)-4-{(Z)-4-phenylsulfanylbut-2-enyloxy}but-2-enyl]methanesulfonamide