Amphoteronolide B

Base Information

• Chemical Name: Amphoteronolide B
• CAS No.: 106799-07-9
• Molecular Formula: C₄₁H₆₂O₁₄
• Molecular Weight: 778.935
• DSSTox Substance ID: DTXSID00910115
• Mol file: 106799-07-9.mol

Synonyms:amphotericin B aglycone;amphoteronolide B

Chemical Property of Amphoteronolide B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.544
• Boiling Point: 1039 °C at 760 mmHg
• Flash Point: 308.4 °C
• PSA: 254.90000
• Density: 1.208g/cm³
• LogP: 1.89350
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 1
• Exact Mass: 778.41395665
• Heavy Atom Count: 55
• Complexity: 1370

Purity/Quality:

99%, ^*data from raw suppliers

AmphoteronolideB(>85%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(C(CCC(CC(CC(=O)OC(C(C1O)C)C)O)O)O)O)O)O)O)C(=O)O)O
• Isomeric SMILES: C[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O
• Uses: Amphoteronolide B is aglycon form of Amphotericin B (A634250) which are polyene macrolide antibiotics.

Technology Process of Amphoteronolide B

There total 8 articles about Amphoteronolide B 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: 80.0%

amphoteronolide B methyl ester → amphoteronolide B (106799-07-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 - 25 ℃; for 1h;

DOI:10.1021/ja00222a027

Reference yield: 50.0%

amphoteronolide B allyl ester (960315-96-2) → amphoteronolide B (106799-07-9)

Guidance literature:

With thiosalicilyc acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 23 ℃; for 15h;

DOI:10.1021/ja075739o

Reference yield:

C43H66O14 → amphoteronolide B (106799-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / CSA / methanol; H₂O / 1 h / Ambient temperature

2: 80 percent / 1N LiOH / H₂O / 1 h / 0 - 25 °C

With lithium hydroxide; camphor-10-sulfonic acid; In methanol; water;

DOI:10.1021/ja00222a029

upstream raw materials:

amphoteronolide B allyl ester

Refernces

• 1、 Palacios, Daniel S.,Anderson, Thomas M.,Burke, Martin D.. "A post-PKS oxidation of the amphotericin B skeleton predicted to be critical for channel formation is not required for potent antifungal activity". . p. 13804 - 13805. Retrieved 2007.