N¹-acetyl-N⁸-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N⁴-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine

Base Information

• Chemical Name: N¹-acetyl-N⁸-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N⁴-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine
• CAS No.: 119860-21-8
• Molecular Formula: C₂₆H₃₂F₂N₄O₈
• Molecular Weight: 566.559

Synonyms:N¹-acetyl-N⁸-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N⁴-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine

Chemical Property of N¹-acetyl-N⁸-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N⁴-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine

Chemical Property:

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Technology Process of N¹-acetyl-N⁸-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N⁴-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine

There total 6 articles about N¹-acetyl-N⁸-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N⁴-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine 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:

acetic anhydride (108-24-7) + [8-Amino-7,7-difluoro-6-hydroxy-5-(4-nitro-benzyloxycarbonylamino)-octyl]-carbamic acid benzyl ester (119860-20-7) → N1-acetyl-N8-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N4-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine (119860-21-8)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; In N,N-dimethyl-formamide; acetonitrile; at -20 - 20 ℃; for 15h; Yield given;

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

Reference yield:

(R,S)-1-formyl-1-(4-nitrobenzyl)-5-benzylpentylene dicarbamate (138802-24-1) → N1-acetyl-N8-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N4-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine (119860-21-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) zinc, iodine / 1.) THF, rt, 15 min, ultrasonication; 2.) THF, rt, 35 min, ultrasonication

2: 89 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

4: trifluoroacetic acid / 1.5 h / 0 °C

5: N-methylmorpholine, isobutylchloroformate / acetonitrile; dimethylformamide / 15 h / -20 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; dimethylsulfide borane complex; ammonia; iodine; sodium hydrogencarbonate; sodium carbonate; trifluoroacetic acid; zinc; isobutyl chloroformate; In diethyl ether; N,N-dimethyl-formamide; acetonitrile;

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

Reference yield:

8-benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-4-(R,S)-(4-nitrobenzyloxycarbonylamino) octanoic acid ethyl ester (119860-17-2) → N1-acetyl-N8-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-N4-(4-nitrobenzyloxycarbonyl)-1,4,8-octanetriamine (119860-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 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

3: trifluoroacetic acid / 1.5 h / 0 °C

4: N-methylmorpholine, isobutylchloroformate / acetonitrile; dimethylformamide / 15 h / -20 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; dimethylsulfide borane complex; ammonia; sodium hydrogencarbonate; sodium carbonate; trifluoroacetic acid; isobutyl chloroformate; In diethyl ether; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

acetic anhydride

[8-Amino-7,7-difluoro-6-hydroxy-5-(4-nitro-benzyloxycarbonylamino)-octyl]-carbamic acid benzyl ester

(R,S)-1-formyl-1-(4-nitrobenzyl)-5-benzylpentylene dicarbamate

8-benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-4-(R,S)-(4-nitrobenzyloxycarbonylamino) octanoic acid ethyl ester

Downstream raw materials:

N-tert-butoxycarbonyl-D-phenylalanyl-N-<1-(3-acetylamino-2,2-difluoro-1-oxo-propyl)-5-tert-butoxycarbonylaminopentyl>-L-prolinamide

N-tert-butoxycarbonyl-D-phenylalanyl-N-<1-(3-acetylamino-2,2-difluoro-1-hydroxy-propyl)-5-benzyloxycarbonylaminopentyl>-L-prolinamide

N₁-Acetyl-N₈-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-1,4,8-octanetriamine

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