tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate

Base Information

• Chemical Name: tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate
• CAS No.: 408341-57-1
• Molecular Formula: C₃₀H₄₄N₂O₁₀
• Molecular Weight: 592.687
• Mol file: 408341-57-1.mol

Synonyms:tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate

Chemical Property of tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate

There total 5 articles about tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-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: 91.0%

tert-butyl (2S)-2-{bis[(tert-butoxy)carbonyl]amino}-5-oxopentanoate (129241-89-0) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate (408341-57-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 5.5h;

DOI:10.1055/s-2002-19295

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate (408341-57-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / DMAP / acetonitrile / 18 h / 20 °C

2: 91 percent / DIBAL / hexane; diethyl ether / 0.25 h / -78 °C

3: 91 percent / DBU / CH₂Cl₂ / 5.5 h / 20 °C

With dmap; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; hexane; dichloromethane; acetonitrile; 3: Horner-Emmons olefination;

DOI:10.1055/s-2002-19295

Reference yield:

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6Z)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)hept-5-enoate (408341-57-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / DCC; DMAP; Et₃N / CH₂Cl₂ / 6 h / 0 - 20 °C

2: 89 percent / DMAP / acetonitrile / 18 h / 20 °C

3: 91 percent / DIBAL / hexane; diethyl ether / 0.25 h / -78 °C

4: 91 percent / DBU / CH₂Cl₂ / 5.5 h / 20 °C

With dmap; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; In diethyl ether; hexane; dichloromethane; acetonitrile; 4: Horner-Emmons olefination;

DOI:10.1055/s-2002-19295

upstream raw materials:

tert-butyl (2S)-2-{bis[(tert-butoxy)carbonyl]amino}-5-oxopentanoate

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

di-tert-butyl dicarbonate

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

Downstream raw materials:

(S,S)-2,6-diaminopimelic acid

(2R,6S)-2,6-diaminoheptanedioic acid

tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6R)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate

tert-butyl (2S)-[bis(tert-butoxycarbonyl)amino]-(6S)-[(benzyloxycarbonyl)amino]-7-(methoxycarbonyl)heptanoate