cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile]

Base Information

• Chemical Name: cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile]
• CAS No.: 267877-02-1
• Molecular Formula: C₄₃H₆₅N₇O₉S
• Molecular Weight: 856.097
• Mol file: 267877-02-1.mol

Synonyms:cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile]

Chemical Property of cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile]

There total 37 articles about cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile] 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: 97.0%

cyclo[Ala-Pro-Phe-Ser(oxaz)-Thr(rprenyl)-Ser(rprenyl)Ile] (245115-73-5) → cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile] (267877-02-1)

Guidance literature:

With hydrogen sulfide; triethylamine; In methanol; at 20 ℃; for 51h;

DOI:10.1016/S0040-4020(03)00294-1

Reference yield:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) → cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile] (267877-02-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 88 percent / diethyl phosphorcyanidate; (i-Pr)2NEt / dimethylformamide; CH₂Cl₂ / 11 h

2: 99 percent / H₂ / Pd/C / ethyl acetate; ethanol / 17 h / 20 °C

3: 79 percent / diethyl phosphorcyanidate; (i-Pr)2NEt / CH₂Cl₂ / 11 h / -5 °C

4: 96 percent / H₂ / Pd/C / ethyl acetate; ethanol / 17 h / 20 °C

5: 3.88 g / diethyl phosphorcyanidate; (i-Pr)2NEt / CH₂Cl₂ / 11 h / -5 °C

6: 90 percent / H₂ / Pd/C / ethyl acetate; ethanol / 20 h / 20 °C

7: 102 mg / PyBOP; (i-Pr)2NEt / CH₂Cl₂ / 16 h / 20 °C

8: 73.6 mg / tris(2-aminoethyl)amine / CH₂Cl₂ / 0.5 h / 20 °C

9: 60.1 mg / Bu₄NOH / tetrahydrofuran / 4 h / 0 °C

10: 7.1 mg / HATU; (i-Pr)2NEt / dimethylformamide / 168 h / 20 °C

11: 5.2 mg / NH₄F; Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

12: 63 percent / DAST / CH₂Cl₂ / 1 h / -20 °C

13: 88 percent / H₂S; Et₃N / methanol / 48 h / 20 °C

With ammonium fluoride; 2,2',2''-triaminotriethylamine; diethyl cyanophosphonate; hydrogen sulfide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrogenolysis / 3: Condensation / 4: Hydrogenolysis / 5: Condensation / 6: Hydrogenolysis / 7: Condensation / 8: carbamate cleavage / 9: ester cleavage / 10: Cyclization / 11: desilylation / 12: Dehydration / 13: Ring cleavage;

DOI:10.1021/jo9914566

Reference yield:

Fmoc-Ala-Pro-OH (186023-44-9) → cyclo[Ala-Pro-PheΨ{(C=S)NH}-Ser-Thr(rprenyl)-Ser(rprenyl)Ile] (267877-02-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 79 percent / diethyl phosphorcyanidate; (i-Pr)2NEt / CH₂Cl₂ / 11 h / -5 °C

2: 96 percent / H₂ / Pd/C / ethyl acetate; ethanol / 17 h / 20 °C

3: 3.88 g / diethyl phosphorcyanidate; (i-Pr)2NEt / CH₂Cl₂ / 11 h / -5 °C

4: 90 percent / H₂ / Pd/C / ethyl acetate; ethanol / 20 h / 20 °C

5: 102 mg / PyBOP; (i-Pr)2NEt / CH₂Cl₂ / 16 h / 20 °C

6: 73.6 mg / tris(2-aminoethyl)amine / CH₂Cl₂ / 0.5 h / 20 °C

7: 60.1 mg / Bu₄NOH / tetrahydrofuran / 4 h / 0 °C

8: 7.1 mg / HATU; (i-Pr)2NEt / dimethylformamide / 168 h / 20 °C

9: 5.2 mg / NH₄F; Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

10: 63 percent / DAST / CH₂Cl₂ / 1 h / -20 °C

11: 88 percent / H₂S; Et₃N / methanol / 48 h / 20 °C

With ammonium fluoride; 2,2',2''-triaminotriethylamine; diethyl cyanophosphonate; hydrogen sulfide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrogenolysis / 3: Condensation / 4: Hydrogenolysis / 5: Condensation / 6: carbamate cleavage / 7: ester cleavage / 8: Cyclization / 9: desilylation / 10: Dehydration / 11: Ring cleavage;

DOI:10.1021/jo9914566

upstream raw materials:

cyclo[Ala-Pro-Phe-Ser(oxaz)-Thr(rprenyl)-Ser(rprenyl)Ile]

N-tert-butoxycarbonyl-L-phenylalanine

(S)-methyl 2-((2S)-2-[(tert-butoxycarbonyl)-3-phenylpropanamido]-3-hydroxy)-propanoate

L-phenylalanyl-L-serine methyl ester hydrochloride

Downstream raw materials:

cyclo[Ala-Pro-Phe-Ser(thiaz)-Thr(rprenyl)-Ser(rprenyl)Ile]