tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate

Base Information

• Chemical Name: tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate
• CAS No.: 1361407-56-8
• Molecular Formula: C₂₃H₃₅NO₈S
• Molecular Weight: 485.599
• Mol file: 1361407-56-8.mol

Synonyms:tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate

Chemical Property of tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate

There total 7 articles about tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate 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: 96.0%

tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-(4-methoxyphenyl)hex-2-enoate (1361407-55-7) + methanesulfonyl chloride (124-63-0) → tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate (1361407-56-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jm2016914

Reference yield:

(3R,4R)-4-[N-(tert-butoxycarbonyl)amino]-5-(4-methoxyphenyl)pent-1-en-3-ol (1361407-53-5) → tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate (1361407-56-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine; dmap / chloroform / 2 h / 0 °C

2.1: dimethylsulfide; ozone / ethyl acetate / 0.5 h / -78 - 0 °C

3.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.33 h / 0 °C / Inert atmosphere

3.2: 3 h / 0 °C / Inert atmosphere

4.1: methanol; potassium carbonate / 2 h / 0 - 20 °C

5.1: triethylamine / dichloromethane / 2 h / 0 °C

With pyridine; methanol; dmap; dimethylsulfide; potassium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In dichloromethane; chloroform; ethyl acetate; acetonitrile; 3.1: Horner-Wadsworth-Emmons olefination / 3.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jm2016914

Reference yield:

C18H25NO6 → tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate (1361407-56-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.33 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 °C / Inert atmosphere

2.1: methanol; potassium carbonate / 2 h / 0 - 20 °C

3.1: triethylamine / dichloromethane / 2 h / 0 °C

With methanol; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In dichloromethane; acetonitrile; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jm2016914

upstream raw materials:

(3R,4R)-4-[N-(tert-butoxycarbonyl)amino]-5-(4-methoxyphenyl)pent-1-en-3-ol

tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)-amino]-6-(4-methoxyphenyl)hex-2-enoate

tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-(4-methoxyphenyl)hex-2-enoate

methanesulfonyl chloride

Downstream raw materials:

tert-butyl (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]-N-[(2-nitrophenyl)sulfonyl]amino]propyl}-5-[N-(tert-butoxycarbonyl)amino]-6-(4-methoxyphenyl)hex-3-enoate

tert-butyl (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]-propyl}-5-[N-(tert-butoxycarbonyl)amino]-6-(4-methoxyphenyl)hex-3-enoate

(2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic acid

tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate