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

Base Information

• Chemical Name: cyclo[Ala-Pro-D-Phe-D-Ser(oxaz)-Thr(rprenyl)-Ser(rprenyl)-Ile]
• CAS No.: 267877-12-3
• Molecular Formula: C₄₃H₆₃N₇O₉
• Molecular Weight: 822.015
• Mol file: 267877-12-3.mol

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

Chemical Property of cyclo[Ala-Pro-D-Phe-D-Ser(oxaz)-Thr(rprenyl)-Ser(rprenyl)-Ile]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclo[Ala-Pro-D-Phe-D-Ser(oxaz)-Thr(rprenyl)-Ser(rprenyl)-Ile]

There total 21 articles about cyclo[Ala-Pro-D-Phe-D-Ser(oxaz)-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: 61.0%

cyclo[Ala-Pro-D-Phe-D-Ser-Thr(rprenyl)-Ser(rprenyl)-Ile] (267877-00-9) → cyclo[Ala-Pro-D-Phe-D-Ser(oxaz)-Thr(rprenyl)-Ser(rprenyl)-Ile] (267877-12-3)

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1021/jo9914566

Reference yield:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) → cyclo[Ala-Pro-D-Phe-D-Ser(oxaz)-Thr(rprenyl)-Ser(rprenyl)-Ile] (267877-12-3)

Guidance literature:

Multi-step reaction with 12 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: 1.78 g / diethyl phosphorcyanidate; (i-Pr)2NEt / CH₂Cl₂ / -5 °C

4: H₂ / Pd/C / ethyl acetate; ethanol

5: 1.59 g / diethyl phosphorcyanidate; (i-Pr)2NEt / CH₂Cl₂ / -5 °C

6: H₂ / Pd/C / ethyl acetate; ethanol

7: 55.1 mg / HATU; (i-Pr)2NEt / dimethylformamide / 20 °C

8: tris(2-aminoethyl)amine / CH₂Cl₂ / 20 °C

9: Bu₄NOH / tetrahydrofuran / 0 °C

10: HATU; (i-Pr)2NEt / CH₂Cl₂ / 72 h / 20 °C

11: 27.9 mg / Bu₄NF; NH₄F / tetrahydrofuran / 20 °C

12: 61 percent / DAST / CH₂Cl₂ / 1 h / -20 °C

With ammonium fluoride; 2,2',2''-triaminotriethylamine; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; hydrogen; 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; 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: Cyclization;

DOI:10.1021/jo9914566

Reference yield:

Fmoc-Ala-Pro-OH (186023-44-9) → cyclo[Ala-Pro-D-Phe-D-Ser(oxaz)-Thr(rprenyl)-Ser(rprenyl)-Ile] (267877-12-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.78 g / diethyl phosphorcyanidate; (i-Pr)2NEt / CH₂Cl₂ / -5 °C

2: H₂ / Pd/C / ethyl acetate; ethanol

3: 1.59 g / diethyl phosphorcyanidate; (i-Pr)2NEt / CH₂Cl₂ / -5 °C

4: H₂ / Pd/C / ethyl acetate; ethanol

5: 55.1 mg / HATU; (i-Pr)2NEt / dimethylformamide / 20 °C

6: tris(2-aminoethyl)amine / CH₂Cl₂ / 20 °C

7: Bu₄NOH / tetrahydrofuran / 0 °C

8: HATU; (i-Pr)2NEt / CH₂Cl₂ / 72 h / 20 °C

9: 27.9 mg / Bu₄NF; NH₄F / tetrahydrofuran / 20 °C

10: 61 percent / DAST / CH₂Cl₂ / 1 h / -20 °C

With ammonium fluoride; 2,2',2''-triaminotriethylamine; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; hydrogen; 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; 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: Cyclization;

DOI:10.1021/jo9914566

upstream raw materials:

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

2-methyl-3-buten-2-ol

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

Fmoc-Ala-Pro-OH

Downstream raw materials:

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