cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-)

Base Information

• Chemical Name: cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-)
• CAS No.: 86066-92-4
• Molecular Formula: C₅₂H₆₂N₈O₉
• Molecular Weight: 943.112
• Mol file: 86066-92-4.mol

Synonyms:cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-)

Chemical Property of cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-)

There total 9 articles about cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-) 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: 76.6%

D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-OH (86048-89-7) → cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-) (86066-92-4)

Guidance literature:

With diphenylphosphoranyl azide; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 - 5 ℃; for 72h;

DOI:10.1021/jo00381a011

Reference yield:

Boc-L-Lys(Z)-OMe (73548-77-3) → cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-) (86066-92-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 92.5 percent / N-methylmorpholine / CH₂Cl₂ / 2 h

2: 100 percent / 2.5 N NaOH, / tetrahydrofuran; H₂O / 6 h

3: N-methylmorpholine / ethyl acetate / 0.2 h / -5 °C

4: N-methylmorpholine / ethyl acetate; dimethylformamide / 1.5 h / -5 °C

5: 2.5 N NaOH / tetrahydrofuran; H₂O / 6 h

6: HCl(gas) / ethyl acetate / 0.75 h / 0 °C

7: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO₃ / dimethylformamide / 72 h / 0 - 5 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; diphenylphosphoranyl azide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00381a011

Reference yield:

Boc-D-Trp-OH (5241-64-5) → cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-) (86066-92-4)

Guidance literature:

Multi-step reaction with 8 steps

1: N-methylmorpholine / CH₂Cl₂ / 0.17 h / -5 °C

2: 92.5 percent / N-methylmorpholine / CH₂Cl₂ / 2 h

3: 100 percent / 2.5 N NaOH, / tetrahydrofuran; H₂O / 6 h

4: N-methylmorpholine / ethyl acetate / 0.2 h / -5 °C

5: N-methylmorpholine / ethyl acetate; dimethylformamide / 1.5 h / -5 °C

6: 2.5 N NaOH / tetrahydrofuran; H₂O / 6 h

7: HCl(gas) / ethyl acetate / 0.75 h / 0 °C

8: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO₃ / dimethylformamide / 72 h / 0 - 5 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; diphenylphosphoranyl azide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00381a011

upstream raw materials:

D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-OH

Boc-L-Lys(Z)-OMe

Boc-D-Trp-OH

C₂₁H₂₈N₂O₆

Downstream raw materials:

MK-678

Refernces