cryptophycin 46

Base Information

• Chemical Name: cryptophycin 46
• CAS No.: 124689-64-1
• Molecular Formula: C35H43 Cl N2 O7
• Molecular Weight: 639.189
• DSSTox Substance ID: DTXSID301046153
• Nikkaji Number: J643.895D
• Wikidata: Q110185808
• ChEMBL ID: CHEMBL13529
• Mol file: 124689-64-1.mol

Synonyms:b-Alanine,N-[3-chloro-N-[5-[(2-hydroxy-4-methyl-1-oxopentyl)oxy]-6-methyl-1-oxo-8-phenyl-2,7-octadienyl]-O-methyl-D-tyrosyl]-2-methyl-,x-lactone,[5S-[1(S*),2E,5R*(R*),6S*,7E]]-; Cryptophycin 3; Cryptophycin C

Chemical Property of cryptophycin 46

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 872.611°C at 760 mmHg
• Flash Point: 481.538°C
• PSA: 127.01000
• Density: 1.134g/cm³
• LogP: 5.85910
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 638.2758794
• Heavy Atom Count: 45
• Complexity: 1040

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CNC(=O)C(NC(=O)C=CCC(OC(=O)C(OC1=O)CC(C)C)C(C)C=CC2=CC=CC=C2)CC3=CC(=C(C=C3)OC)Cl
• Isomeric SMILES: C[C@@H]1CNC(=O)[C@H](NC(=O)/C=C/C[C@H](OC(=O)[C@@H](OC1=O)CC(C)C)[C@H](C)/C=C/C2=CC=CC=C2)CC3=CC(=C(C=C3)OC)Cl

Technology Process of cryptophycin 46

There total 61 articles about cryptophycin 46 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: 64.0%

(S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(3-chloro-4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester; compound with trifluoro-acetic acid → cryptophycin C (124689-64-1)

Guidance literature:

With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 2.5h;

DOI:10.1021/ja00114a011

Reference yield:

cryptophycin-17 + methyl iodide (74-88-4) → cryptophycin C (124689-64-1)

Guidance literature:

With potassium carbonate; In acetone; at 70 ℃; for 4h;

DOI:10.1021/ja00154a002

Reference yield:

(R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid (162465-45-4) → cryptophycin C (124689-64-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 87.5 mg / 1-hydroxybenzotriazole; triethylamine; 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran; CH₂Cl₂ / 0 - 20 °C

2: hydrogen / Pd(OH)2 on carbon / ethyl acetate / 2 h / 20 °C

3: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH₂Cl₂ / 18 h / 20 °C

4: CH₂Cl₂ / 0 - 20 °C

5: 31.0 mg / NaHCO₃; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C

With dmap; N-[3-(diethylamino)propyl]-N'-ethylcarbodiimide hydrochloride; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; diisopropyl-carbodiimide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: coupling / 2: Hydrogenolysis / 3: Esterification / 4: Hydrolysis / 5: Cyclization;

DOI:10.1021/jo9907585

upstream raw materials:

cryptophycin-30

methyl iodide

(S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid

tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

Downstream raw materials:

cryptophycin-1

cryptophycin-27

cryptophycin-31