992-65-4

Usage

Uses

Used in Pharmaceutical Industry:
Erythromycin A N-oxide is used as a metabolite of erythromycin A for its potential biological activity and applications in the development of new antibiotics or as a precursor for the synthesis of other erythromycin derivatives. Its ability to revert to erythromycin A under reducing conditions may also have implications for drug delivery and targeting strategies.

InChI:InChI=1/C37H67NO14/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(52-34-28(40)24(38(11,12)46)15-19(3)48-34)21(5)29(22(6)33(43)50-25)51-26-17-36(9,47-13)31(42)23(7)49-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

Upstream product

• 114-07-8 erythromycin 
• 138505-44-9 (9S)-9-dihydroerythromycin A N-oxide 
• 992-62-1 N-Demethylerythromycin A 
• 15562-19-3 9S-Dihydroerythronolide A aglycon 
• 138505-34-7 (9S)-9-dihydro-9,11-O-isopropylideneerythronolide A 
• 138505-32-5 (9S)-9-dihydro-3,5-O-(p-methoxybenzylidene)erythronolide A 
• 138505-33-6 (9S)-9-dihydro-9,11-O-isopropylidene-3,5-O-(p-methoxybenzylidene)erythronolide 
• 138505-35-8 (9S)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide 
• 138505-36-9 (9S)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-oxide 
• 138505-43-8 (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide 
• 138505-42-7 (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide 
• 137101-04-3 methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranoside 
• 168072-11-5 phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-β-L-altro-pyranoside 
• 138603-63-1 1-(2-pyrimidinethio) 3,4,6-trideoxy-2-O-methoxycarbonyl-3-(dimethylamino)-D-xylo-hexopyranoside 

Downstream Products

• 118074-07-0 6-O-methylerythromycin A N-oxide 
• 114-07-8 erythromycin 

Relevant academic research and scientific papers

Evaluation of the efficiency of the macrolactonization using MNBA in the synthesis of erythromycin a aglycon

Various intermediates for the synthesis of erythronolide A, an aglycon of erythromycin A, are prepared from the corresponding seco-acids using 2-methyl-6-nitrobenzoic anhydride (MNBA) in the presence of 4-(dimethylamino)pyridine (DMAP) with or without tri

PREPARATION AND UTILITY OF SUBSTITUTED ERYTHROMYCIN ANALOGS

The present disclosure is directed to novel macrolide antibiotics of Formula 1 and pharmaceutically acceptable salts and prodrugs thereof; and the chemical syntheses and medical uses of these novel macrolide antibiotics for the treatment and/or management of infections caused by various aerobic and anaerobic gram-positive and gram-negative microorganisms as well as various mycobacteria.

Method of preparing clarithromycin

Clarithromycin can be easily prepared by reacting erythromycin A N-oxide with a methylating agent to obtain 6-O-methylerythromycin A N-oxide; and treating 6-O-methylerythromycin A N-oxide obtained above with a reducing agent in a high yield.

SYNTHESIS OF ERYTHROMYCIN RELATED MACROLIDES

The synthesisand characterization of a number of macrolides, structurally related with erythromycin, is described.These derivatives have been previously investigated for thier ability to induce contractions and to displace bound motilin in rabbit duodenum.

Preparation of (8S)-8-fluoroerythromycins with N-F fluorinating agents

(8S)-8-fluoroerythromycins are prepared by reacting 8,9-anhydroerythromycin 6,9-hemiacetals or an N-oxide thereof with a carboxylic acid and an N-F fluorinating agent. The anhydro starting material may be prepared in situ from erythromycins or an N-oxide

Application of highly stereocontrolled glycosidations employing 2,6-anhydro-2-thio sugars to the syntheses of erythromycin A and olivomycin A trisaccharide

The highly efficient syntheses of the erythromycin A (1) from its aglycon, (9S)-9-dihydroerythronolide A (4), and the C-D-E trisaccharide 3 of olivomycin A have been accomplished by the successful application of stereocontrolled glycosidations using 2,6-anhydro-2-thio sugars. The former synthesis includes the highly α-stereoselective glycosidation of the C5 desosaminated lactone 12 with phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-L-altropyranos ide (10), which was achieved by using NIS-TfOH. The latter synthesis involves both the highly β-stereoselective glycosidation of 1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose (23), which was realized by employing TMSOTf, and the highly α-stereoselective glycosidation of phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl- 1,2-dithio-L-manno-pyranoside (24), which succeeded by utilizing NBS. Hydrogenolyses using Raney Ni as a catalyst and selective deprotections of the key glyco substances 17 and 22 led to the total syntheses of erythromycin A (1) and the C-D-E trisaccharide 3 of olivomycin A, respectively.

Application of efficient glycosylation of 2,6-anhydro-2-thio sugar to the total synthesis of erythromycin A

The total synthesis of erythromycin A (1) from (9S)-9-dihydroerythronolide A (2) was achieved efficiently by the highly stereoselective and powerful glycosylation of 2,6-anhydro-2-thio sugar 9 as a key step.