Patellamide A

Base Information

• Chemical Name: Patellamide A
• CAS No.: 81120-73-2
• Molecular Formula: C₃₅H₅₀N₈O₆S₂
• Molecular Weight: 742.964
• DSSTox Substance ID: DTXSID101001791
• Nikkaji Number: J825.416H
• Wikipedia: Patellamide_A
• Wikidata: Q7144428
• Metabolomics Workbench ID: 169291
• ChEMBL ID: CHEMBL448385
• Mol file: 81120-73-2.mol

Synonyms:patellamide A

Chemical Property of Patellamide A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 995°C at 760 mmHg
• Flash Point: 555.5°C
• PSA: 255.80000
• Density: 1.44g/cm³
• LogP: 3.65590
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 742.32947369
• Heavy Atom Count: 51
• Complexity: 1370

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: other cyclic peptide,other cyclic peptide (Cyanobactin)
• Canonical SMILES: CCC(C)C1C2=NC(CO2)C(=O)NC(C3=NC(=CS3)C(=O)NC(C4=NC(C(O4)C)C(=O)NC(C5=NC(=CS5)C(=O)N1)C(C)C)C(C)CC)C(C)C
• Isomeric SMILES: CC[C@H](C)[C@H]1C2=N[C@@H](CO2)C(=O)N[C@@H](C3=NC(=CS3)C(=O)N[C@H](C4=N[C@@H]([C@H](O4)C)C(=O)N[C@@H](C5=NC(=CS5)C(=O)N1)C(C)C)[C@@H](C)CC)C(C)C

Technology Process of Patellamide A

There total 15 articles about Patellamide A 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: 73.0%

C35H51ClN8O6S2 (103929-30-2) → C35H50N8O6S2 (81120-73-2)

Guidance literature:

With silver trifluoromethanesulfonate; In benzene; for 6h; Heating;

DOI:10.1016/S0040-4039(00)99037-3

Reference yield:

D-(val)Thz-OMe (103929-32-4) → C35H50N8O6S2 (81120-73-2)

Guidance literature:

Multi-step reaction with 10 steps

1: diethyl phosphorocyanidate, triethylamine / dimethylformamide

2: 4N hydrogen chloride / dioxane / 1 h / Ambient temperature

3: 85 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide

4: 4N hydrogen chloride / dioxane / 1 h / Ambient temperature

5: 79 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide

6: 1N NaOH / dimethylformamide

7: 4N hydrogen chloride / dioxane / 1 h / Ambient temperature

8: 55 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide

9: thionyl chloride / 48 h / 4 °C

10: 73 percent / silver trifluoromethanesulfonate / benzene / 6 h / Heating

With hydrogenchloride; sodium hydroxide; thionyl chloride; diethyl cyanophosphonate; silver trifluoromethanesulfonate; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)99037-3

Reference yield:

Boc-D-(val)Thz-OMe (100803-69-8,106930-60-3) → C35H50N8O6S2 (81120-73-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) TFA, 2.) NaHCO₃

2: diethyl phosphorocyanidate, triethylamine / dimethylformamide

3: 4N hydrogen chloride / dioxane / 1 h / Ambient temperature

4: 85 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide

5: 4N hydrogen chloride / dioxane / 1 h / Ambient temperature

6: 79 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide

7: 1N NaOH / dimethylformamide

8: 4N hydrogen chloride / dioxane / 1 h / Ambient temperature

9: 55 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide

10: thionyl chloride / 48 h / 4 °C

11: 73 percent / silver trifluoromethanesulfonate / benzene / 6 h / Heating

With hydrogenchloride; sodium hydroxide; thionyl chloride; diethyl cyanophosphonate; silver trifluoromethanesulfonate; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; In 1,4-dioxane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)99037-3

upstream raw materials:

C₃₅H₅₁ClN₈O₆S₂

Boc-(S)-Ser-(R)-Val-Thz-OMe

Boc-L-aThr-D-(val)Thz-OMe

Boc-L-Ile-L-aThr-D-(val)Thz-OH

Refernces