Latrunculin M

Base Information

• Chemical Name: Latrunculin M
• CAS No.: 122876-49-7
• Molecular Formula: C₂₁H₃₃NO₅S
• Molecular Weight: 411.563
• Nikkaji Number: J2.428.484K
• Mol file: 122876-49-7.mol

Synonyms:Latrunculin M;122876-49-7;methyl (S,2Z,6Z)-10-((2S,6R)-6-hydroxy-6-((R)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-3,8-dimethyldeca-2,6-dienoate;C21-H33-N-O5-S;AKOS040752434;methyl (2Z,6Z,8S)-10-[(2S,6R)-6-hydroxy-6-[(4R)-2-oxo-1,3-thiazolidin-4-yl]oxan-2-yl]-3,8-dimethyldeca-2,6-dienoate;2,6-Decadienoic acid, 3,8-dimethyl-10-(tetrahydro-6-hydroxy-6-(2-oxo-4- thiazolidinyl)-2H-pyran-2-yl)-, methyl ester, (2S-(2alpha(2Z,6Z,8R*),6beta,6(S*)))-

Chemical Property of Latrunculin M

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.151g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 411.20794433
• Heavy Atom Count: 28
• Complexity: 606

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC1CCCC(O1)(C2CSC(=O)N2)O)C=CCCC(=CC(=O)OC)C
• Isomeric SMILES: C[C@@H](CC[C@@H]1CCC[C@@](O1)([C@@H]2CSC(=O)N2)O)/C=C\CC/C(=C\C(=O)OC)/C

Technology Process of Latrunculin M

There total 3 articles about Latrunculin M 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:

13-Deoxy-15-methoxy-13,O-seco-Lat B Carboxylic Acid (122877-06-9) → Lat M (122876-49-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / AcOH / H₂O; tetrahydrofuran / 1 h / 70 °C

2: diethyl ether / 3 h / Ambient temperature

With acetic acid; In tetrahydrofuran; diethyl ether; water;

Reference yield:

15-Methoxy-Lat B (105917-28-0) → Lat M (122876-49-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 16 percent / Et₃SiH, Et₂O-BF₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 44 percent / AcOH / H₂O; tetrahydrofuran / 1 h / 70 °C

3: diethyl ether / 3 h / Ambient temperature

With triethylsilane; boron trifluoride diethyl etherate; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water;

Reference yield:

13-Deoxy-13,O-seco-Lat B Carboxylic Acid (122877-07-0) → Lat M (122876-49-7)

Guidance literature:

In diethyl ether; for 3h; Ambient temperature;

upstream raw materials:

13-Deoxy-13,O-seco-Lat B Carboxylic Acid

13-Deoxy-15-methoxy-13,O-seco-Lat B Carboxylic Acid

15-Methoxy-Lat B

Refernces