3225-82-9

Basic information

• Product Name: erythronolide B
• Synonyms: erythronolide B;(3R)-3α,5α,7β,9β,11α,13β-Hexamethyl-4β,6β,7,12β-tetrahydroxy-14β-ethyl-1-oxacyclotetradecane-2,10-dione;12-Deoxyerythronolide A
• CAS NO: 3225-82-9
• Molecular Formula: C₂₁H₃₈O₇
• Molecular Weight: 402.52222
• Mol File: 3225-82-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 576.2°Cat760mmHg
• Flash Point: 192.2°C
• Appearance: /
• Density: 1.069g/cm³
• Vapor Pressure: 1.12E-15mmHg at 25°C
• Refractive Index: 1.473
• PKA: 13.81±0.70(Predicted)
• CAS DataBase Reference: erythronolide B(CAS DataBase Reference)
• NIST Chemistry Reference: erythronolide B(3225-82-9)
• EPA Substance Registry System: erythronolide B(3225-82-9)

Safety Data

• Hazardous Substances Data: 3225-82-9(Hazardous Substances Data)

Usage

General Description

Erythronolide B is a polyketide compound derived from natural sources and is an essential precursor in the biosynthesis of the macrolide antibiotic erythromycin. It consists of a 14-membered macrolactone ring with several hydroxyl and methyl groups. Erythronolide B is a crucial intermediate in the biosynthetic pathway of erythromycin, and its structure and modifications have been extensively studied for the development of new antibiotics and other bioactive compounds. The compound has garnered attention for its potential therapeutic applications in treating bacterial infections and has served as a model for the synthesis of various macrolide antibiotics. Its intricate molecular structure and biological activities have made erythronolide B a subject of significant interest in medicinal chemistry and drug development.

InChI:InChI=1/C21H38O7/c1-8-15-11(3)17(23)12(4)16(22)10(2)9-21(7,27)19(25)13(5)18(24)14(6)20(26)28-15/h10-15,17-19,23-25,27H,8-9H2,1-7H3/t10-,11+,12+,13+,14-,15-,17+,18+,19-,21-/m1/s1

Upstream product

• 11038-52-1 (9S)-dihydroerythronolide B 
• 114114-29-3 (2R,4R)-4-[(4S,5S,6S)-6-((1S,2R)-2-Hydroxy-1-methyl-butyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentan-2-ol 
• 56014-68-7 (1S,2R,5R,6R,7R,8S,9S,10R,12R,13R,15R,17S)-5-Ethyl-7,9,12-trihydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one 
• 114137-93-8 (2S,3R,4S)-3-Benzenesulfinyl-4-[(2S,4R,5R,6R)-6-[(1R,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentan-2-ol 
• 114114-45-3 {(1R,2R)-2-[(2S,4R,5R,6R)-6-[(S)-2-((R)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-ethyl-propoxy}-tert-butyl-diphenyl-silane 
• 114181-58-7 {(1R,2R)-2-[(2S,4R,5R,6R)-6-[(S)-2-((S)-Benzenesulfinyl)-1-methyl-ethyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-ethyl-propoxy}-tert-butyl-diphenyl-silane 
• 123219-39-6 (2S,3R,4S)-4-[(2S,4R,5R,6R)-6-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-3-phenylsulfanyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentan-2-ol 
• 114114-43-1 (S)-3-[(2S,4R,5R,6R)-6-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1,1,1-triphenyl-butan-2-one 
• 123219-40-9 (2R,4R)-4-[(2R,4S,5S,6R)-6-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentan-2-ol 
• 114137-92-7 tert-Butyl-{(1R,2R)-1-ethyl-2-[(2S,4R,5R,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-propoxy}-diphenyl-silane 
• 114114-46-4 (R)-2-((4S,5S,6R)-6-{(1R,3R)-1-Hydroxy-3-[(2R,4S,5S,6S)-6-((1S,2R)-2-hydroxy-1-methyl-butyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-methyl-butyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid 
• 114114-44-2 (R)-2-[(2R,4S,5S,6R)-6-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propan-1-ol 
• 114114-29-3 (2R,4R)-4-[(2R,4S,5S,6S)-6-((1S,2R)-2-Hydroxy-1-methyl-butyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentan-2-ol 
• 114114-34-0 1-[(4R,5S,6R)-2,2,5-Trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-ethanone 

Downstream Products

• 17867-95-7 O¹¹-benzoyl-O³,O⁵-phenylboranediyl-12-deoxy-erythronolide-A 
• 17867-93-5 O¹¹-acetyl-O³,O⁵-phenylboranediyl-12-deoxy-erythronolide-A 
• 19270-26-9 10-epi-erythronolide B 
• 17867-92-4 O³,O⁵-phenylboranediyl-12-deoxy-erythronolide-A 

Relevant articles and documents

Frontiers and opportunities in chemoenzymatic synthesis

Natural product biosynthetic pathways have evolved enzymes with myriad activities that represent an expansive array of chemical transformations for constructing secondary metabolites. Recently, harnessing the biosynthetic potential of these enzymes through chemoenzymatic synthesis has provided a powerful tool that often rivals the most sophisticated methodologies in modern synthetic chemistry and provides new opportunities for accessing chemical diversity. Herein, we describe our research efforts with enzymes from a broad collection of biosynthetic systems, highlighting recent progress in this exciting field.

SYNTHESIS OF MACROLIDE ANTIBIOTICS. 15. STEREODIRECTED SYNTHESIS OF ERYTHRONOLIDE B ACCORDING TO THE COUPLING SCHEME OF THE (C9-C13) + (C7-C8) + (C1-C6) FRAGMENTS

-

TOTAL SYNTHESIS OF ERYTHRONOLIDE B. 1. SKELETON ASSEMBLY IN (C9-C13) + (C7-C8) + (C1-C6) SEQUENCE.

Erythronolide B has been synthesized starting from levoglucosan.