benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate

Base Information

• Chemical Name: benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate
• CAS No.: 880144-45-6
• Molecular Formula: C₂₉H₃₆F₂N₂O₈
• Molecular Weight: 578.61
• Mol file: 880144-45-6.mol

Synonyms:benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate

Chemical Property of benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate

There total 6 articles about benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate 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: 87.0%

benzyl (2R,5E)-2-[bis(tert-butoxycarbonyl)amino]-6-nitrohex-5-enoate (784156-33-8) + (2,3-difluorophenyl)boronic acid (121219-16-7) → benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate (880144-45-6)

Guidance literature:

With water; sodium carbonate; η4-1,5-cyclooctadiene-μ-2,4-pentanedionato-iridium(I); (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In 1,4-dioxane; at 20 - 35 ℃; for 6h; Alkaline aqueous solution;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate (880144-45-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methanol; hexane; dichloromethane / 1 h / 0 °C

1.2: 24 h / 20 °C

2.1: diisobutylaluminium hydride / diethyl ether; toluene / 0.58 h / -78 - -65 °C

2.2: 0.5 h / -65 - 20 °C

3.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C

3.2: 1.5 h / 0 - 20 °C

4.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere

4.2: 6 h / 20 - 35 °C

With diisobutylaluminium hydride; N,N,N',N'-tetramethylguanidine; In 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; toluene;

Reference yield:

1-benzyl 5-methyl N,N-bis(tert-butoxycarbonyl)-D-glutamate (784156-32-7) → benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate (880144-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / diethyl ether; toluene / 0.58 h / -78 - -65 °C

1.2: 0.5 h / -65 - 20 °C

2.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C

2.2: 1.5 h / 0 - 20 °C

3.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere

3.2: 6 h / 20 - 35 °C

With diisobutylaluminium hydride; N,N,N',N'-tetramethylguanidine; In 1,4-dioxane; diethyl ether; water; toluene;

upstream raw materials:

benzyl (2R,5E)-2-[bis(tert-butoxycarbonyl)amino]-6-nitrohex-5-enoate

(2,3-difluorophenyl)boronic acid

di-tert-butyl dicarbonate

1-benzyl 5-methyl N,N-bis(tert-butoxycarbonyl)-D-glutamate

Downstream raw materials:

(5S)-N₂,N₂-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-D-lysine

tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamate

(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one

di-tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-1-(2-hydroxy-2-methylpropyl)-2-oxoazepan-3-yl]imidodicarbonate