Cbz-Thr(TBDMS)-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce

Base Information

• Chemical Name: Cbz-Thr(TBDMS)-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce
• CAS No.: 188585-92-4
• Molecular Formula: C₄₇H₆₃Cl₃N₄O₁₀Si
• Molecular Weight: 978.483
• Mol file: 188585-92-4.mol

Synonyms:Cbz-Thr(TBDMS)-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce

Chemical Property of Cbz-Thr(TBDMS)-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cbz-Thr(TBDMS)-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce

There total 18 articles about Cbz-Thr(TBDMS)-(E)ΔMeTyr(MOM)-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: 21.2%

Cbz-Thr(TBDMS)-(Z)ΔMeTyr(MOM)-Leu-D-Phe-OTce (188585-91-3) → Cbz-Thr(TBDMS)-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce (188585-92-4)

Guidance literature:

In acetone; toluene; at 0 ℃; for 1.5h; Irradiation;

DOI:10.1248/cpb.45.236

Reference yield:

4-methoxymethoxy-benzaldehyde (6515-21-5) → Cbz-Thr(TBDMS)-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce (188585-92-4)

Guidance literature:

Multi-step reaction with 12 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

With 1H-imidazole; benzenesulfonamide; dmap; potassium hydroxide; sodium hydroxide; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; In 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(TBDMS)-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce (188585-92-4)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; benzenesulfonamide; dmap; potassium hydroxide; sodium hydroxide; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.45.236

upstream raw materials:

Cbz-Thr(TBDMS)-(Z)ΔMeTyr(MOM)-Leu-D-Phe-OTce

4-methoxymethoxy-benzaldehyde

4-hydroxy-benzaldehyde

O-methoxymethyl-β-hydroxytyrosine

Downstream raw materials:

Cbz-Thr-(E)ΔMeTyr(MOM)-Leu-D-Phe-OTce

C₅₉H₇₁N₉O₁₇

WS₉₃₂₆A

Refernces