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

Base Information

• Chemical Name: Cbz-Thr[Boc-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OTce
• CAS No.: 188585-95-7
• Molecular Formula: C₅₈H₇₀Cl₃N₇O₁₅
• Molecular Weight: 1211.59
• Mol file: 188585-95-7.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 22 articles about Cbz-Thr[Boc-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OTce 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:

4-methoxymethoxy-benzaldehyde (6515-21-5) → Cbz-Thr[Boc-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OTce (188585-95-7)

Guidance literature:

Multi-step reaction with 16 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

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; 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-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OTce (188585-95-7)

Guidance literature:

Multi-step reaction with 17 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

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; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.45.236

Reference yield:

O-methoxymethyl-β-hydroxytyrosine (125774-95-0) → Cbz-Thr[Boc-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OTce (188585-95-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 1 N aq. NaOH / 0.33 h / 90 °C

2: 85 percent / BSA / CH₂Cl₂ / 5 h / 0 - 20 °C

3: 32.1 percent / diethyl ether; ethyl acetate / 0.17 h

4: 93.6 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

5: 72.1 percent / thiophenol, TFA / CH₂Cl₂ / 0.5 h / 0 °C

6: 49.1 percent / 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline / CH₂Cl₂ / 14 h / Ambient temperature

7: DBU / toluene / 2.5 h / Ambient temperature

8: 98 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

9: 87.3 percent / NaOH / methanol / 48 h / 30 °C

10: 32.6 percent / Et₃N, EEDQ / CH₂Cl₂ / 33 h / Ambient temperature

11: 21.2 percent / acetone; toluene / 1.5 h / 0 °C / Irradiation

12: 99.9 percent / 67percent AcOH / 28 h / 25 °C

13: 86.5 percent / EDC*HCl, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

14: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature

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

With 1H-imidazole; hydrogenchloride; benzenesulfonamide; dmap; 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; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.45.236

upstream raw materials:

4-methoxymethoxy-benzaldehyde

4-hydroxy-benzaldehyde

O-methoxymethyl-β-hydroxytyrosine

O-methoxymethyl-N-methyl-β-hydroxytyrosine

Downstream raw materials:

WS₉₃₂₆A

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

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

Refernces