Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OH

Base Information

• Chemical Name: Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OH
• CAS No.: 188585-97-9
• Molecular Formula: C₆₀H₇₆N₈O₁₇
• Molecular Weight: 1181.31
• Mol file: 188585-97-9.mol

Synonyms:

Chemical Property of Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OH

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OH

There total 24 articles about Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OH 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: 82.6%

Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OTce (188585-96-8) → Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OH (188585-97-9)

Guidance literature:

With acetic acid; zinc; Ambient temperature;

DOI:10.1248/cpb.45.236

Reference yield:

4-methoxymethoxy-benzaldehyde (6515-21-5) → Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OH (188585-97-9)

Guidance literature:

Multi-step reaction with 19 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

With 1H-imidazole; hydrogenchloride; benzenesulfonamide; dmap; potassium hydroxide; sodium hydroxide; 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) → Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OH (188585-97-9)

Guidance literature:

Multi-step reaction with 20 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

With 1H-imidazole; hydrogenchloride; benzenesulfonamide; dmap; potassium hydroxide; sodium hydroxide; 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[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OTce

4-methoxymethoxy-benzaldehyde

4-hydroxy-benzaldehyde

O-methoxymethyl-β-hydroxytyrosine

Downstream raw materials:

WS₉₃₂₆A

C₅₉H₇₁N₉O₁₇

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

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

Refernces