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

Base Information

Chemical Name:N-tert-butoxycarbonyl-D-phenylalanyl-N-<1-(3-acetylamino-2,2-difluoro-1-oxo-propyl)-5-tert-butoxycarbonylaminopentyl>-L-prolinamide
CAS No.:129476-12-6
Molecular Formula:C₃₄H₅₁F₂N₅O₈
Molecular Weight:695.804
Hs Code.:

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

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

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

There total 9 articles about N-tert-butoxycarbonyl-D-phenylalanyl-N-<1-(3-acetylamino-2,2-difluoro-1-oxo-propyl)-5-tert-butoxycarbonylaminopentyl>-L-prolinamide 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:

: 138802-24-1
(R,S)-1-formyl-1-(4-nitrobenzyl)-5-benzylpentylene dicarbamate

: 129476-12-6
N-tert-butoxycarbonyl-D-phenylalanyl-N-<1-(3-acetylamino-2,2-difluoro-1-oxo-propyl)-5-tert-butoxycarbonylaminopentyl>-L-prolinamide

Guidance literature:: Multi-step reaction with 8 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

6: tin(II) chloride / ethanol / 2 h / Heating

8: 2.) pyridinium dichromate, 3 Angstroem molecular sieves, glacial acetic acid / 2.) CH₂Cl₂, rt, 15 h

With 4-methyl-morpholine; hydrogenchloride; dipyridinium dichromate; dimethylsulfide borane complex; 3 A molecular sieve; ammonia; iodine; sodium hydrogencarbonate; sodium carbonate; acetic acid; trifluoroacetic acid; tin(ll) chloride; zinc; isobutyl chloroformate; In diethyl ether; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0040-4020(95)00896-G

Reference yield:

: 119860-17-2
8-benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-4-(R,S)-(4-nitrobenzyloxycarbonylamino) octanoic acid ethyl ester

: 129476-12-6
N-tert-butoxycarbonyl-D-phenylalanyl-N-<1-(3-acetylamino-2,2-difluoro-1-oxo-propyl)-5-tert-butoxycarbonylaminopentyl>-L-prolinamide

Guidance literature:: Multi-step reaction with 7 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

5: tin(II) chloride / ethanol / 2 h / Heating

7: 2.) pyridinium dichromate, 3 Angstroem molecular sieves, glacial acetic acid / 2.) CH₂Cl₂, rt, 15 h

With 4-methyl-morpholine; hydrogenchloride; dipyridinium dichromate; dimethylsulfide borane complex; 3 A molecular sieve; ammonia; sodium hydrogencarbonate; sodium carbonate; acetic acid; trifluoroacetic acid; tin(ll) chloride; isobutyl chloroformate; In diethyl ether; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0040-4020(95)00896-G

Reference yield:

: N-α-(4-nitrobenzyloxycarbonyl)-N-ε-benzyloxycarbonyl lysine methyl ester

: 129476-12-6
N-tert-butoxycarbonyl-D-phenylalanyl-N-<1-(3-acetylamino-2,2-difluoro-1-oxo-propyl)-5-tert-butoxycarbonylaminopentyl>-L-prolinamide

Guidance literature:: Multi-step reaction with 9 steps

1: 77 percent / diisobutylaluminium hydride / diethyl ether; toluene; hexane / 0.17 h / -78 °C

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

3: 89 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

5: trifluoroacetic acid / 1.5 h / 0 °C

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

7: tin(II) chloride / ethanol / 2 h / Heating

9: 2.) pyridinium dichromate, 3 Angstroem molecular sieves, glacial acetic acid / 2.) CH₂Cl₂, rt, 15 h

With 4-methyl-morpholine; hydrogenchloride; dipyridinium dichromate; dimethylsulfide borane complex; 3 A molecular sieve; ammonia; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; acetic acid; trifluoroacetic acid; tin(ll) chloride; zinc; isobutyl chloroformate; In diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/0040-4020(95)00896-G