H-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser υ-lactone

Base Information

• Chemical Name: H-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser υ-lactone
• CAS No.: 188585-99-1
• Molecular Formula: C₄₀H₅₄N₈O₁₂
• Molecular Weight: 838.915
• Mol file: 188585-99-1.mol

Synonyms:

Chemical Property of H-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser υ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of H-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser υ-lactone

There total 28 articles about H-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser υ-lactone 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: 74.9%

Cbz-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser(Bzl) υ-lactone (188585-98-0) → H-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser υ-lactone (188585-99-1)

Guidance literature:

With pyridine; hydrogen fluoride; methoxybenzene; for 1h; Ambient temperature;

DOI:10.1248/cpb.45.236

Reference yield:

4-methoxymethoxy-benzaldehyde (6515-21-5) → H-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser υ-lactone (188585-99-1)

Guidance literature:

Multi-step reaction with 23 steps

1: KOH / ethanol / 19 h / Ambient temperature

2: 1 N aq. NaOH / 0.33 h / 90 °C

3: 85 percent / BSA / CH₂Cl₂ / 5 h / 0 - 20 °C

4: 32.1 percent / diethyl ether; ethyl acetate / 0.17 h

5: 93.6 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

6: 72.1 percent / thiophenol, TFA / CH₂Cl₂ / 0.5 h / 0 °C

7: 49.1 percent / 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline / CH₂Cl₂ / 14 h / Ambient temperature

8: DBU / toluene / 2.5 h / Ambient temperature

9: 98 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

10: 87.3 percent / NaOH / methanol / 48 h / 30 °C

11: 32.6 percent / Et₃N, EEDQ / CH₂Cl₂ / 33 h / Ambient temperature

12: 21.2 percent / acetone; toluene / 1.5 h / 0 °C / Irradiation

13: 99.9 percent / 67percent AcOH / 28 h / 25 °C

14: 86.5 percent / EDC*HCl, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

15: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature

16: Et₃N, HOBT, EDC*HCl / CH₂Cl₂ / 1 h / Ambient temperature

17: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature

18: Et₃N, HOBT, EDC*HCl / CH₂Cl₂ / 8 h / Ambient temperature

19: 82.6 percent / Zn, 90percent AcOH / Ambient temperature

20: EDC*HCl / CH₂Cl₂; dimethylformamide / Ambient temperature

21: TFA, anisole / 0.5 h / Ambient temperature

22: pyridine / dimethylformamide / 16 h / Ambient temperature

23: 74.9 percent / HF, pyridine, anisole / 1 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; benzenesulfonamide; dmap; potassium hydroxide; sodium hydroxide; hydrogen fluoride; benzotriazol-1-ol; acetic acid; thiophenol; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; zinc; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.45.236

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → H-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser υ-lactone (188585-99-1)

Guidance literature:

Multi-step reaction with 24 steps

1: 88.7 percent / Et₃N / tetrahydrofuran / 1 h / Ambient temperature

2: KOH / ethanol / 19 h / Ambient temperature

3: 1 N aq. NaOH / 0.33 h / 90 °C

4: 85 percent / BSA / CH₂Cl₂ / 5 h / 0 - 20 °C

5: 32.1 percent / diethyl ether; ethyl acetate / 0.17 h

6: 93.6 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

7: 72.1 percent / thiophenol, TFA / CH₂Cl₂ / 0.5 h / 0 °C

8: 49.1 percent / 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline / CH₂Cl₂ / 14 h / Ambient temperature

9: DBU / toluene / 2.5 h / Ambient temperature

10: 98 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

11: 87.3 percent / NaOH / methanol / 48 h / 30 °C

12: 32.6 percent / Et₃N, EEDQ / CH₂Cl₂ / 33 h / Ambient temperature

13: 21.2 percent / acetone; toluene / 1.5 h / 0 °C / Irradiation

14: 99.9 percent / 67percent AcOH / 28 h / 25 °C

15: 86.5 percent / EDC*HCl, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

16: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature

17: Et₃N, HOBT, EDC*HCl / CH₂Cl₂ / 1 h / Ambient temperature

18: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature

19: Et₃N, HOBT, EDC*HCl / CH₂Cl₂ / 8 h / Ambient temperature

20: 82.6 percent / Zn, 90percent AcOH / Ambient temperature

21: EDC*HCl / CH₂Cl₂; dimethylformamide / Ambient temperature

22: TFA, anisole / 0.5 h / Ambient temperature

23: pyridine / dimethylformamide / 16 h / Ambient temperature

24: 74.9 percent / HF, pyridine, anisole / 1 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; benzenesulfonamide; dmap; potassium hydroxide; sodium hydroxide; hydrogen fluoride; benzotriazol-1-ol; acetic acid; thiophenol; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.45.236

upstream raw materials:

Cbz-Thr-(E)ΔMeTyr-Leu-D-Phe-allo-Thr-Asn-Ser(Bzl) υ-lactone

4-methoxymethoxy-benzaldehyde

Boc-D-Phe-OH

4-hydroxy-benzaldehyde

Downstream raw materials:

WS₉₃₂₆A

Refernces