Amphotericin B methyl ester

Base Information

• Chemical Name: Amphotericin B methyl ester
• CAS No.: 36148-89-7
• Molecular Formula: C48H75 N O17
• Molecular Weight: 938.12
• UNII: 074Z98YIW3
• DSSTox Substance ID: DTXSID701009331
• Wikidata: Q27225718
• Metabolomics Workbench ID: 66944
• ChEMBL ID: CHEMBL321176
• Mol file: 36148-89-7.mol

Synonyms:AME;amphotericin B methyl ester;metamphocin;methylamphotericin B;methylamphotericin B acetate;methylamphotericin B hydrochloride;SQ 20,627

Chemical Property of Amphotericin B methyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1102.6°Cat760mmHg
• PKA: 12.25±0.70(Predicted)
• Flash Point: 620.6°C
• PSA: 308.61000
• Density: g/cm³
• LogP: 1.50040
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 4
• Exact Mass: 937.50349992
• Heavy Atom Count: 66
• Complexity: 1680

Purity/Quality:

99% ^*data from raw suppliers

Amphotericin B Methyl Ester ^*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)OC)OC3C(C(C(C(O3)C)O)N)O
• Isomeric SMILES: C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=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)OC)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)O
• Uses: Amphotericin B Methyl Ester is the methyl ester derivative of the polyene antibiotic Amphotericin B (A634250). Amphotericin B Methyl Esterin is a cholesterol binding compound that showed inhibiton of human immunodeficiency virus type 1 (HIV-1).

Technology Process of Amphotericin B methyl ester

There total 4 articles about Amphotericin B methyl ester 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: 86.0%

N-FMOC amphotericin B methyl ester (127970-82-5) → amphotericin B methyl ester (36148-89-7)

Guidance literature:

With piperidine;

DOI:10.1016/S0960-894X(97)10180-9

Reference yield:

C55H83N3O17 → amphotericin B methyl ester (36148-89-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / HS(CH₂)3SH, Et₃N / methanol / 24 h / 25 °C

2: 1.) CSA; 2.) H₂O / 1.) MeOH, 25 deg C, 2 h; 2.) MeOH, 25 deg C, 4 h

With 1.3-propanedithiol; camphor-10-sulfonic acid; water; triethylamine; In methanol;

DOI:10.1021/ja00243a043

Reference yield:

C55H85NO17 → amphotericin B methyl ester (36148-89-7)

Guidance literature:

With camphor-10-sulfonic acid; water; Yield given. Multistep reaction; 1.) MeOH, 25 deg C, 2 h; 2.) MeOH, 25 deg C, 4 h;

DOI:10.1021/ja00243a043

upstream raw materials:

N-FMOC amphotericin B methyl ester

AmBisome

Downstream raw materials:

AmBisome

Refernces

• 1、 Nicolaou, K. C.,Daines, R. A.,Chakraborty, T. K.,Ogawa, Y.. "Total Synthesis of Amphotericin B". . p. 2821 - 2822. Retrieved 2007/10/02.