26754-37-0

Usage

Uses

Used in Pharmaceutical Industry:
Erythronolide A is used as an intermediate in the synthesis of erythromycin and related antibiotics for the treatment of bacterial infections. Its unique structure and properties make it a valuable compound in the development of new antibiotics with improved efficacy and reduced side effects.
Used in Medicinal Chemistry Research:
Erythronolide A is used as a research compound in medicinal chemistry to explore its potential applications in drug discovery and development. Its structure and properties provide insights into the design of new macrolide antibiotics and other bioactive compounds with therapeutic potential.
Used in Biosynthetic Pathway Studies:
Erythronolide A is used in studies of the biosynthetic pathways of polyketides, providing insights into the mechanisms of antibiotic production in microorganisms. Understanding these pathways can help in the development of novel strategies for the production of antibiotics and other bioactive compounds.
Used in Drug Resistance Research:
Erythronolide A is used in research aimed at understanding and overcoming antibiotic resistance. Its structure and mode of action can provide valuable information on the development of new antibiotics that can combat resistant bacterial strains.

InChI:InChI=1/C21H38O8/c1-8-14-21(7,28)18(25)11(3)15(22)10(2)9-20(6,27)17(24)12(4)16(23)13(5)19(26)29-14/h10-14,16-18,23-25,27-28H,8-9H2,1-7H3/t10-,11+,12+,13-,14-,16+,17-,18-,20-,21-/m1/s1

Upstream product

• 105545-16-2 (1S,2R,5R,6S,7R,8R,10R,12R,13R,17S)-5-Ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione 
• 863663-37-0 (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-2,9-dihydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one 
• 863663-28-9 (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one 
• 863663-36-9 3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol 
• 863663-27-8 3,5-O-benzylidene-2,4,7-trideoxy-6-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-2,4-dimethyl-3,5-O-(1-methylethylidene)-6-O-(triethylsilyl)-L-glycero-D-gulo-heptitol 
• 863663-35-8 3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-C-((2R)-2-{(4S,5R)-4-methyl-5-[(1Z)-1-methylbut-1-en-1-yl]-4,5-dihydroisoxazol-3-yl}propyl)-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol 
• 863663-26-7 3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol 
• 99285-07-1 3,5:9,11-di-O-isopropylidene.(9S)-9-deoxo-hydroxyerythronolide 
• 105545-13-9 (R)-2-((4S,5S,6R)-6-{(1R,3R)-3-[(4S,5S,6R)-6-((1R,2R)-1,2-Dihydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-hydroxy-1-methyl-butyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid 
• 124928-80-9 1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-ethanol 
• 105544-93-2 5-O-benzyl-1,6,7-trideoxy-3,4-O-isopropylidene-4-C-methyl-keto-D-arabino-2-heptulose 
• 124928-82-1 5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol 
• 105544-92-1 3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol 
• 105545-08-2 (2S,3R,4S,5R,6R,8R,9S,10S,11R,12R,13R)-2,4,6,8,10,12-Hexamethyl-6,12-bis-triethylsilanyloxy-pentadecane-1,3,5,9,11,13-hexaol 

Downstream Products

• 15562-19-3 (9R)-dihydroerythronolide 
• 15562-19-3 9S-Dihydroerythronolide A aglycon 

Relevant academic research and scientific papers

Preparation method and application of 14-membered ring and 16-membered ring macrolide derivatives

The invention provides a preparation method and application of 14-membered ring and 16-membered ring macrolide derivatives. Experiments prove that the prepared 14-membered ring and 16-membered ring macrolide derivatives are medicines with specific intestinal motility promoting activity and without antibiotic activity. According to the preparation method and the application of the 14-membered ringand 16-membered ring macrolide derivatives, the 14-membered ring and 16-membered ring macrolide derivatives have a very good effect of promoting the digestive tract motility and can enhance the intestinal peristalsis, increase the defecation amount and speed up passing of intestinal contents.

Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies

(Chemical Equation Presented) An expeditious synthesis of erythronolide A is documented. Key steps of the approach include two magnesium-mediated nitrile oxide cycloadditions, a chelation-controlled Grignard reaction, and a Sharpless asymmetric dihydroxylation. 2009 American Chemical Society.

Total synthesis of erythronolide A by MgII-mediated cycloadditions of nitrile oxides

(Chemical Equation Presented) A cycloaddition comes of age: The focal points of a stereoselective total synthesis of erythronolide A (see structure) are two MgII-mediated cycloadditions of nitrile oxides. Of broader significance, the strategy not only facilitates the synthesis of specific polyketide targets (i.e. natural products) but also opens up new possibilities for the preparation of non-natural analogues.

STEREO-CONTROLLED SYNTHESIS OF ERYTHRONOLIDES A AND B FROM 1,6-ANHYDRO-β-D-GLUCOPYRANOSE (LEVOGLUCOSAN). SKELETON ASSEMBLY IN (C9 - C13) + (C7 - C8) + (C1 - C6) SEQUENCE

Stereospecific syntheses of erythronolides A and B have been accomplished starting from 1,6-anhydro-β-D-glucopyranose (levoglucosan) in a uniform synthetic sequence.