527-75-3

Basic information

• Product Name: ERYTHROMYCIN B (150 MG)
• Synonyms: ERYTHROMYCIN B (150 MG);12-deoxy-erythromyci;12-deoxyerythromycin;abbot24091;berythromycin;Erythromycin B (100 mg);12-DeoxyerythroMycin, BerythroMycin
• CAS NO: 527-75-3
• Molecular Formula: C₃₇H₆₇NO₁₂
• Molecular Weight: 717.931
• Mol File: 527-75-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 191-195 °C
• Boiling Point: 807.578°C at 760 mmHg
• Flash Point: 442.207°C
• Appearance: /
• Density: 1.176g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.527
• PKA: 13.49±0.70(Predicted)
• CAS DataBase Reference: ERYTHROMYCIN B (150 MG)(CAS DataBase Reference)
• NIST Chemistry Reference: ERYTHROMYCIN B (150 MG)(527-75-3)
• EPA Substance Registry System: ERYTHROMYCIN B (150 MG)(527-75-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 527-75-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 527-75-3 differently. You can refer to the following data:
1. Erythromycin B (12-deoxyerythromycin A) is a minor co-metabolite of erythromycin produced Saccharopolyspora erythreae. Erythromycin B exhibits broad spectrum antibiotic activity, albeit less potent than erythromycin A. Erythromycin B played an integral part of the SAR studies of semi-synthetic erythromycins, however none reached clinical development.
2. Erythromycin B is a co-metabolite of Erythromycin A (E649950), an antibacterial agent.

InChI:InChI=1/C37H67NO12/c1-14-26-20(4)29(40)21(5)28(39)18(2)16-36(9,44)33(50-35-30(41)25(38(11)12)15-19(3)46-35)22(6)31(23(7)34(43)48-26)49-27-17-37(10,45-13)32(42)24(8)47-27/h18-27,29-33,35,40-42,44H,14-17H2,1-13H3/t18-,19-,20+,21-,22+,23-,24+,25+,26+,27+,29+,30-,31+,32+,33-,35+,36-,37-/m1/s1

Upstream product

• 608143-20-0 (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-(benzyloxymethoxy)-6-[triethylsilyloxy]-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,3,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanoic acid 
• 944740-95-8 5-(4-dimethylamino-3-methoxycarbonyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-8-[6-(2-hydroxy-1-methyl-butyl)-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-2,4,6-trimethyl-6-triethylsilanyloxy-nonanoic acid 
• 608143-21-1 (9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B 
• 188786-47-2 (9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B 
• 944740-76-5 (3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadec-1-en-4-ol 
• 188786-09-6 (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane 
• 188786-19-8 (3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene 
• 188786-14-3 (2R,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-4-[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecanal 
• 188786-24-5 (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-6-[(tert-butyldimethylsilyl)-oxy]-13-hydroxy-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanoic acid 
• 188786-61-0 (9S)-3-O-(α-L-cladinosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide B 
• 188785-95-7 (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane 
• 188785-99-1 (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonan-7-one 
• 188786-05-2 (2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one 
• 944740-86-7 (9S)-3-O-(α-L-cladinosyl)-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide B 

Downstream Products

• 21395-58-4 Erythromycin-B-N-oxid 
• 134628-59-4 C₄₇H₇₇NO₁₄ 
• 150785-53-8 ABT-229 
• 134628-60-7 C₄₇H₇₅NO₁₃ 
• 134628-59-4 C₄₇H₇₇NO₁₄ 

Relevant articles and documents

Total synthesis of erythromycin B

We report the details of the first total synthesis of erythromycin B using two different strategies for the end game. The first of these follows a classical approach in which the desosamine and cladinose residues are sequentially appended to a macrocyclic lactone, which was formed by cyclization of a seco acid derivative, to give a bis-glycosylated macrolide intermediate that is converted into erythromycin B. The second strategy features an abiotic approach in which a seco acid bearing a desosamine residue is cyclized to give a monoglycosylated macrocyclic lactone that is then transformed into erythromycin B via a sequence of steps involving refunctionalizations and a glycosylation to introduce the cladinose moiety. Attempts to prepare a bis-glycosylated seco acid by de novo synthesis were unsuccessful. The syntheses of the key seco acid intermediates feature the oxidative transformation of a furan containing C(3)-C(10) to provide a dioxabicyclo[3.3.1]nonenone that served as a template on which to create the stereocenters at C(6) and C(8). A stereoselective aldol reaction was used to establish the C(11)-C(15) segment, and a stereoselective crotylation was implemented to introduce the propionate subunit comprising C(1)-C(2).

C 8 epimeric 10,11-anhydroerythromycins A and the C 8 epimeric 11,12-epoxyerythromycins A.

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