N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide

Base Information

• Chemical Name: N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide
• CAS No.: 459144-52-6
• Molecular Formula: C₂₄H₃₆INO₅SSi
• Molecular Weight: 605.61
• Mol file: 459144-52-6.mol

Synonyms:N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide

Chemical Property of N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide

There total 4 articles about N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide 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: 29.0%

N-[(2Z)-2-iodo-2-butenyl]-p-toluenesulfonamide (459144-49-1) + methyl (2Z,4E)-6-bromo-3-tert-butyldimethylsiloxy-2,4-hexadienoate (459144-40-2) → N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide (459144-52-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo0258397

Reference yield:

(E)-3-Oxo-hex-4-enoic acid methyl ester (147086-20-2) → N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide (459144-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

2: 58 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / Heating

3: 29 percent / sodium hydride / dimethylformamide / 20 °C

With dmap; N-Bromosuccinimide; sodium hydride; triethylamine; dibenzoyl peroxide; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0258397

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N-[(Z)-2-iodobutenyl]-N-[(2E,4E)-4-tert-butyldimethylsilyloxy-5-methoxycarbonyl-2,4-pentadienyl]-p-toluenesulfonamide (459144-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

2: 58 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / Heating

3: 29 percent / sodium hydride / dimethylformamide / 20 °C

With dmap; N-Bromosuccinimide; sodium hydride; triethylamine; dibenzoyl peroxide; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0258397

upstream raw materials:

N-[(2Z)-2-iodo-2-butenyl]-p-toluenesulfonamide

methyl (2Z,4E)-6-bromo-3-tert-butyldimethylsiloxy-2,4-hexadienoate

(E)-3-Oxo-hex-4-enoic acid methyl ester

tert-butyldimethylsilyl chloride