cyclo(glycyl-phenylalanyl-prolyl-N-(beta)-(tert-butoxycarbonyl)-alpha,beta-diaminopropanyoly)

Base Information

Chemical Name:cyclo(glycyl-phenylalanyl-prolyl-N-(beta)-(tert-butoxycarbonyl)-alpha,beta-diaminopropanyoly)
CAS No.:77100-18-6
Molecular Formula:C24H33 N5 O6
Molecular Weight:487.55
Hs Code.:
Mol file:77100-18-6.mol

Synonyms:Cyclic[3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanylglycyl-L-phenylalanyl-D-prolyl];Pyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine, cyclic peptide deriv.

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Chemical Property of cyclo(glycyl-phenylalanyl-prolyl-N-(beta)-(tert-butoxycarbonyl)-alpha,beta-diaminopropanyoly)

Chemical Property:

Vapor Pressure:1.15E-26mmHg at 25°C
Boiling Point:815.4°C at 760 mmHg
PKA:11.79±0.46(Predicted)
Flash Point:446.9°C
PSA：145.94000
Density:1.276g/cm³
LogP:1.15940

Purity/Quality:

Safty Information:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

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Technology Process of cyclo(glycyl-phenylalanyl-prolyl-N-(beta)-(tert-butoxycarbonyl)-alpha,beta-diaminopropanyoly)

There total 10 articles about cyclo(glycyl-phenylalanyl-prolyl-N-(beta)-(tert-butoxycarbonyl)-alpha,beta-diaminopropanyoly) 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: 14.5%

: 77087-66-2
(S)-2-({(R)-1-[(S)-2-(2-Amino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid 2,4,5-trichloro-phenyl ester

: 77100-18-6
cyclo(glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoyl)

Guidance literature:: With pyridine; In N,N-dimethyl-formamide; at 90 ℃; for 8h;
DOI:10.1021/jm00137a017

Reference yield:

: 1070-19-5
N-(tert-butyloxycarbonyl) azide

: 77100-18-6
cyclo(glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoyl)

Guidance literature:: Multi-step reaction with 10 steps

1: 88.4 percent / 1 N aq. NaoH / dioxane / 48 h / 45 °C

2: Na, NH₃(liq.) / 0.17 h / -50 °C

3: 61 percent / 4 N aq. NaOH / 2 h / 25 °C / pH 10-10.5

4: 79.5 percent / diethyl ether

5: 100 percent / H₂ / 10percent Pd/C / methanol / 24 h

6: 72 percent / DCC, HOBt / CH₂Cl₂ / 4 °C

7: 1 N KOH / ethanol; H₂O / 0.17 h

8: DCC, pyridine / 1.) 4 deg C, 20 h, 2.) 25 deg C, 1 h

9: 84 percent / acetic acid, H₂ / 10percent Pd/C / methanol / 3 h / 0 °C / 760 Torr

10: 14.5 percent / pyridine / dimethylformamide / 8 h / 90 °C

With pyridine; potassium hydroxide; sodium hydroxide; ammonia; hydrogen; sodium; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00137a017

Reference yield:

: 58457-98-0
methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate

: 77100-18-6
cyclo(glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoyl)

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / H₂ / 10percent Pd/C / methanol / 24 h

2: 72 percent / DCC, HOBt / CH₂Cl₂ / 4 °C

3: 1 N KOH / ethanol; H₂O / 0.17 h

4: DCC, pyridine / 1.) 4 deg C, 20 h, 2.) 25 deg C, 1 h

5: 84 percent / acetic acid, H₂ / 10percent Pd/C / methanol / 3 h / 0 °C / 760 Torr

6: 14.5 percent / pyridine / dimethylformamide / 8 h / 90 °C

With pyridine; potassium hydroxide; hydrogen; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00137a017