SE2RF5V7VG

Base Information

• Chemical Name: SE2RF5V7VG
• CAS No.: 71968-02-0
• Molecular Formula: C₂₄H₃₅NO₄
• Molecular Weight: 401.546
• Hs Code.: 29419000
• UNII: SE2RF5V7VG
• Nikkaji Number: J2.732.744C
• Wikidata: Q105006303
• Mol file: 71968-02-0.mol

Synonyms:aspochalasin D

Chemical Property of SE2RF5V7VG

Chemical Property:

• Vapor Pressure: 2.68E-17mmHg at 25°C
• Boiling Point: 607.6°C at 760 mmHg
• PKA: 13.10±0.70(Predicted)
• Flash Point: 321.2°C
• PSA: 86.63000
• Density: 1.15g/cm³
• LogP: 3.26170
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 401.25660860
• Heavy Atom Count: 29
• Complexity: 765

Purity/Quality:

98% ^*data from raw suppliers

Aspochalasin D ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(NC(=O)C23C(C=C(CCC(C(C=CC3=O)O)O)C)C=C1C)CC(C)C
• Isomeric SMILES: C[C@H]1[C@H]2[C@@H](NC(=O)[C@@]23[C@@H](/C=C(/CC[C@H]([C@H](/C=C/C3=O)O)O)\C)C=C1C)CC(C)C
• Description: Aspochalasin D is a co-metabolite originally isolated from A. microcysticus with aspochalasins A, B, and C, that was initially thought to be inactive. It has antibacterial activity against Gram-positive and Gram-negative bacteria at a concentration of 1 mg/ml. Aspochalasin D is more cytotoxic, via apoptosis, to Ba/F3-V12 cells in an IL-3-free medium than in an IL-3-containing medium (IC50s = 0.49 and 1.9 μg/ml, respectively).

Technology Process of SE2RF5V7VG

There total 42 articles about SE2RF5V7VG 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: 99.0%

C36H63NO4Si2 → aspochalasin D (71968-02-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 30 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201808481

Reference yield: 90.0%

(17S,18S)-17,18-isopropylidenedioxy-14-methyl-10-prop-2'-yl-<11>cytochalasa-6(7),13Z,19E-triene-1,21-dione (124575-53-7) → isoaspochalasin C (71968-02-0,72401-79-7)

Guidance literature:

With hydrogenchloride; In methanol; water; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)83439-6

Reference yield:

ethyl 3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate (140836-86-8,124575-39-9) → isoaspochalasin C (71968-02-0,72401-79-7)

Guidance literature:

Multi-step reaction with 14 steps

1: DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

2: 72 percent / benzene / 16 h / Heating

3: 88 percent / H₂ / Pd/C / ethyl acetate

5: 97 percent / NaOH / ethanol; H₂O / 1.5 h / Ambient temperature

6: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature

7: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C

8: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C

9: H₂O₂, m-chloroperoxybenzoic acid / CHCl₃; H₂O / 0.75 h / -50 - 0 °C

10: toluene / 5 h / 90 °C

11: NaOH / methanol / 2 h / Ambient temperature

12: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h

13: 58 percent / H₂O₂ / pyridine; CH₂Cl₂; H₂O / 18 h / Ambient temperature

14: 90 percent / HCl / methanol; H₂O / 1 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; chloro-trimethyl-silane; oxalyl dichloride; hydrogen; dihydrogen peroxide; lithium isopropylamide; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; chloroform; water; ethyl acetate; toluene; benzene;

DOI:10.1016/S0040-4020(01)83439-6

upstream raw materials:

(17S,18S)-17,18-isopropylidenedioxy-14-methyl-10-prop-2'-yl-<11>cytochalasa-6(7),13Z,19E-triene-1,21-dione

(S)-2-amino-4-methylpentan-1-ol

(4R)-4-amino-6-methylheptanoic acid

ethyl 3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate