Tryptoquivaline

Base Information

• Chemical Name: Tryptoquivaline
• CAS No.: 55387-45-6
• Molecular Formula: C₂₉H₃₀N₄O₇
• Molecular Weight: 546.58
• UNII: CW5S8OP3VO
• DSSTox Substance ID: DTXSID90970728
• Nikkaji Number: J12.800G
• Wikidata: Q27275854
• Metabolomics Workbench ID: 103863
• ChEMBL ID: CHEMBL2386536
• Mol file: 55387-45-6.mol

Synonyms:fumitremorgin C;tryproquivaline D (2'S-(2'alpha,9'alpha(4R*(S*)),9'abeta))-isomer;tryproquivaline L (9'R-(9'alpha(R*),9'abeta))-isomer;tryproquivaline L (9'R-(9'alpha(S*),9'abeta))-isomer;tryproquivaline M (2'S-(2'alpha,9'alpha(4R*(S*)),9'abeta))-isomer;tryproquivaline M (2'S-(2'alpha,9'alpha(4S*(S*)),9'abeta))-isomer;tryproquivaline N (2'S-(2'alpha,9'alpha(R*),9'abeta))-isomer;tryptoquivaline

Chemical Property of Tryptoquivaline

Chemical Property:

• Melting Point: 215 °C (water)
• PSA: 131.27000
• LogP: 3.19920
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 546.21144931
• Heavy Atom Count: 40
• Complexity: 1150

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(C1=NC2=CC=CC=C2C(=O)N1C3CC4(C5N(C6=CC=CC=C64)C(=O)C(N5O)(C)C)OC3=O)OC(=O)C
• Isomeric SMILES: CC(C)[C@@H](C1=NC2=CC=CC=C2C(=O)N1[C@@H]3C[C@]4([C@H]5N(C6=CC=CC=C64)C(=O)C(N5O)(C)C)OC3=O)OC(=O)C

Technology Process of Tryptoquivaline

There total 10 articles about Tryptoquivaline 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: 93.0%

deoxytryptoquivaline (60676-57-5) → tryptoquivaline (55387-45-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(01)91189-X

Reference yield:

(R)-2-(2-Amino-benzoylamino)-3-(1H-indol-3-yl)-propionic acid benzyl ester (94141-26-1) → tryptoquivaline (55387-45-6)

Guidance literature:

Multi-step reaction with 7 steps

1: molecular sieves 4A, TsOH / CH₂Cl₂ / Ambient temperature

2: KF, 18-crown-6, EtN(i-Pr)2 / acetonitrile / 4 h / 35 °C

3: DDQ / CHCl₃ / 3 h / 30 °C

4: H₂ / Pd/C

5: N-iodosuccinimide, trifluoroacetic acid / 50 °C

6: Zn, AcOH

7: m-CPBA

With potassium fluoride; N-iodo-succinimide; 18-crown-6 ether; 4 A molecular sieve; hydrogen; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; palladium on activated charcoal; In dichloromethane; chloroform; acetonitrile;

Reference yield:

(R)-2-[2-((S)-1-Acetoxy-2-methyl-propyl)-4-oxo-4H-quinazolin-3-yl]-3-{1-[2-methyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionyl]-1H-indol-3-yl}-propionic acid benzyl ester (94141-34-1) → tryptoquivaline (55387-45-6)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd/C

2: N-iodosuccinimide, trifluoroacetic acid / 50 °C

3: Zn, AcOH

4: m-CPBA

With N-iodo-succinimide; hydrogen; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc; palladium on activated charcoal;

upstream raw materials:

deoxytryptoquivaline

deoxytryptoquivaline

(R)-2-(2-Amino-benzoylamino)-3-(1H-indol-3-yl)-propionic acid benzyl ester

(R)-2-[2-((S)-1-Acetoxy-2-methyl-propyl)-4-oxo-4H-quinazolin-3-yl]-3-{1-[2-methyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionyl]-1H-indol-3-yl}-propionic acid