N⁴-(4-nitrobenzyloxycarbonyl)-N¹-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine

Base Information

• Chemical Name: N⁴-(4-nitrobenzyloxycarbonyl)-N¹-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine
• CAS No.: 173918-54-2
• Molecular Formula: C₃₁H₃₅F₂N₃O₈
• Molecular Weight: 615.631

Synonyms:N⁴-(4-nitrobenzyloxycarbonyl)-N¹-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine

Chemical Property of N⁴-(4-nitrobenzyloxycarbonyl)-N¹-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine

Chemical Property:

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Technology Process of N⁴-(4-nitrobenzyloxycarbonyl)-N¹-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine

There total 4 articles about N⁴-(4-nitrobenzyloxycarbonyl)-N¹-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine 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:

(R,S)-N-(4-nitrobenzyloxycarbonyl)-O-benzyl-tyrosinal (173918-49-5) → N4-(4-nitrobenzyloxycarbonyl)-N1-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine (173918-54-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 46 percent / zinc / tetrahydrofuran / reflux; rt, 15 h

2: 57 percent / ammonia gas / diethyl ether / -78 °C

3: 1.) BH₃(CH₃)2S; 2.) sat.hydrogen chloride; 3.) NaHCO₃, Na₂CO₃, / 1.) THF, reflux, 4 h; 2.) Et₂O, 0.45 min; 3.) water/THF, rt, 15 h

With hydrogenchloride; dimethylsulfide borane complex; ammonia; sodium hydrogencarbonate; sodium carbonate; zinc; In tetrahydrofuran; diethyl ether;

DOI:10.1016/0040-4020(95)00896-G

Reference yield:

(R,S)-N-(4-nitrobenzyloxycarbonyl)-O-benzyl-tyrosine methyl ester → N4-(4-nitrobenzyloxycarbonyl)-N1-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine (173918-54-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 51 percent / ddisobutylaluminium hydride / diethyl ether; toluene; hexane / 0.17 h / -78 °C

2: 46 percent / zinc / tetrahydrofuran / reflux; rt, 15 h

3: 57 percent / ammonia gas / diethyl ether / -78 °C

4: 1.) BH₃(CH₃)2S; 2.) sat.hydrogen chloride; 3.) NaHCO₃, Na₂CO₃, / 1.) THF, reflux, 4 h; 2.) Et₂O, 0.45 min; 3.) water/THF, rt, 15 h

With hydrogenchloride; dimethylsulfide borane complex; ammonia; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; zinc; In tetrahydrofuran; diethyl ether; hexane; toluene;

DOI:10.1016/0040-4020(95)00896-G

Reference yield:

4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester (173918-50-8) → N4-(4-nitrobenzyloxycarbonyl)-N1-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine (173918-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / ammonia gas / diethyl ether / -78 °C

2: 1.) BH₃(CH₃)2S; 2.) sat.hydrogen chloride; 3.) NaHCO₃, Na₂CO₃, / 1.) THF, reflux, 4 h; 2.) Et₂O, 0.45 min; 3.) water/THF, rt, 15 h

With hydrogenchloride; dimethylsulfide borane complex; ammonia; sodium hydrogencarbonate; sodium carbonate; In diethyl ether;

DOI:10.1016/0040-4020(95)00896-G

upstream raw materials:

di-tert-butyl dicarbonate

4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)pentanamide

(R,S)-N-(4-nitrobenzyloxycarbonyl)-O-benzyl-tyrosinal

4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester

Downstream raw materials:

[4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

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