36148-89-7

Basic information

• Product Name: AmphotericinB
• Synonyms: Methylamphotericin B;Aids000095;Aids-000095;Amb;Ame;Amphotericin B monomethyl ester;Amphotericin B, methyl ester;AMphotericin B Methyl Ester 90%
• CAS NO: 36148-89-7
• Molecular Formula: C₄₈H₇₅NO₁₇
• Molecular Weight: 938.1056
• Mol File: 36148-89-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 1102.6°Cat760mmHg
• Flash Point: 620.6°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.25±0.70(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: AmphotericinB(CAS DataBase Reference)
• NIST Chemistry Reference: AmphotericinB(36148-89-7)
• EPA Substance Registry System: AmphotericinB(36148-89-7)

Safety Data

• Hazardous Substances Data: 36148-89-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

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).

Definition

ChEBI: The methyl ester of amphotericin B.

InChI:InChI=1/C48H75NO17/c1-28-18-16-14-12-10-8-6-7-9-11-13-15-17-19-35(65-47-45(59)42(49)44(58)31(4)64-47)25-39-41(46(60)62-5)38(55)27-48(61,66-39)26-34(52)22-32(50)20-21-36(53)37(54)23-33(51)24-40(56)63-30(3)29(2)43(28)57/h6-19,28-39,41-45,47,50-55,57-59,61H,20-27,49H2,1-5H3/b7-6-,10-8-,11-9-,14-12-,15-13-,18-16-,19-17-/t28-,29+,30-,31+,32-,33+,34-,35-,36-,37-,38-,39-,41+,42-,43+,44+,45-,47-,48+/m0/s1

Synthetic route

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

Conditions	Yield
With piperidine	86%

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

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

AmBisome (1397-89-3) → amphotericin B methyl ester (36148-89-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) pyridine / 1.) DMF, methanol, room temperature, 4 h, 2.) DMF, methanol, room temperature, 30 min 2: 86 percent / piperidine View Scheme

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

Conditions	Yield
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 View Scheme

amphotericin B methyl ester (36148-89-7) → AmBisome (1397-89-3)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water at 25℃; for 1h;	80%

3′-N-Fmoc-AmB (127970-81-4) + amphotericin B methyl ester (36148-89-7) → C110H156N2O35

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	62%

amphotericin B methyl ester (36148-89-7) + (9H-fluoren-9-yl)methyl(2-oxoethyl)carbamate (156939-62-7) → C50H80N2O17

Conditions	Yield
Stage #1: amphotericin B methyl ester; (9H-fluoren-9-yl)methyl(2-oxoethyl)carbamate With sodium cyanoborohydride In methanol; N,N-dimethyl-formamide at 20℃; for 18h; Stage #2: With piperidine In methanol; dimethyl sulfoxide at 24℃; for 1h; Further stages.;	31%

amphotericin B methyl ester (36148-89-7) → C111H213NO21Si10

Conditions	Yield
With ozone; triphenylphosphine 1.) CH2Cl2, methanol, -78 deg C, 2.) CH2Cl2, methanol, -78 deg C -> room temperature, overnight; Yield given. Multistep reaction;

N-(9-fluorenylmethoxycarbonyl)glycyl-3-aminopropanal (911368-25-7) + amphotericin B methyl ester (36148-89-7) → C53H85N3O18

Conditions	Yield
Stage #1: N-(9-fluorenylmethoxycarbonyl)glycyl-3-aminopropanal; amphotericin B methyl ester With sodium tris(acetoxy)borohydride In N,N-dimethyl-formamide; isopropyl alcohol at 20℃; for 5.5h; Stage #2: With piperidine In methanol; dimethyl sulfoxide at 24℃; for 0.5h; Further stages.;

Upstream product

• 127970-82-5 N-FMOC amphotericin B methyl ester 
• 1397-89-3 AmBisome 

Downstream Products

• 1397-89-3 AmBisome 

Relevant articles and documents

Synthesis and biological evaluation of non-polyene analogs of amphotericin B

Synthesis of the first analog of a polyene macrolide antibiotic containing a rigid, non-polyene backbone has been accomplished. The sterol recognition surface of amphotericin B has been modified in an effort to better understand the role of the polyene backbone. Its antifungal activity is reduced significantly compared with amphotericin B.