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205110-48-1

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205110-48-1 Usage

Description

Cethromycin (formerly ABT-773) is a ketolide antibiotic originally developed by Abbott in the late 1990s, but abandoned in 2002. Since 2004, Advanced Life Sciences has promoted current development of cethromycin. The ketolides are structurally derived from erythromycin A and are designed to overcome resistance to macrolides. One of the main features is the lack of the neutral sugar L-cladinose at position 3 of the erythonolide ring, which is replaced by a keto group (thus giving rise to the class name). Lack of the L-cladinose moiety results in better drug absorption and less gastric irritation through improved acid stability.

Physical properties

Cethromycin is a 6-O-ketolide, meaning that, compared with 11-Nketolides such as telithromycin, linkage with the macrolactone ring is in the 6-O-position, with an O-propylallyl linkage replacing the aminopropyl linkage of telithromycin. Cethromycin presents as a white crystalline powder. As yet, cethromycin has been used only in clinical trials and is not available for clinical use. Development is primarily directed at upper and lower respiratory tract infections.

Uses

Antibacterial.

Biological Activity

Oral bioavailability of cethromycin has been poorly studied in humans. Animal studies report values ranging from approximately 36% to 50%. Absorption of cethromycin appears to be dose dependent with time to Cmax increasing from 0.9 to 5.1 hours with increasing dosage. Food does not appear to exert meaningful effects on the pharmacokinetics of cethromycin, but this aspect deserves additional study. In a study on the effects of drug co-administration on the pharmacokinetics of cethromycin, ranitidine was found to significantly reduce cethromycin Cmax concentrations, by 25.7%. Conversely, sucralfate had no effect on cethromycin concentrations. The degree of serum protein binding is considered to approach 90%.

Mechanism of action

The mechanism of action is similar to macrolides and is based on interaction with the peptidyl transferase site of the 50S ribosomal subunit, thus inhibiting the translation of rRNAs and preventing the elongation step of protein synthesis. In addition, cethromycin also interferes at an earlier stage of protein synthesis by disrupting the assembling of 50S subunit precursors to block the formation of a functional 50S subunit. Ketolides in general (including cethromycin) inhibit protein synthesis by binding to the 50S ribosomal subunit, close to the peptidyl transferase site at the entrance of the ribosomal exit tunnel. The presence of a 3-keto group in place of the L-cladinose moiety, common to all ketolides, allows cethromycin to bind to the ribosomal target in the 23S rRNA domain V without causing expression of ribosomal mutations. The additional flexible side chain (in the 6-O position for cethromycin) attached to the macrocyclic ring allows binding to an additional ribosomal site. This dual binding affinity increases the binding affinity of cethromycin several-fold compared with that of erythromycin. It is probably also responsible for overcoming resistance mediated by both the ribosomal mutations (erm) and efflux pump (mef) mechanisms. This leads to an enhanced activity against S. pneumoniae, including most of the macrolide-resistant strains. Conversely, the methoxy group at position C-6 provides greater acid stability than that of other macrolides, and is related to greater gastrointestinal stability.

Drug interactions

Ketolides and macrolides are substrates and inhibitors of the cytochrome P450 (CYP450) 3A4 system. So far, data available specifically for cethromycin are very limited and mainly exist in abstract form. It is expected that interactions are similar to other drugs that are involved in this pathway. This is exemplified by ketoconazole, a potent CYP3A4 inhibitor that caused a 5-fold increase in cethromycin AUC and a 2.5-fold increase in drug Cmax, although cethromycin’s main metabolite showed a decreased Cmax but no effect on its AUC. Similarly, rifampicin (600 mg) significantly affected the pharmacokinetics of cethromycin (300 mg), with a 95% reduction in the ketolide’s AUC and its metabolite N-desmethyl cethromycin.

Check Digit Verification of cas no

The CAS Registry Mumber 205110-48-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,5,1,1 and 0 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 205110-48:
(8*2)+(7*0)+(6*5)+(5*1)+(4*1)+(3*0)+(2*4)+(1*8)=71
71 % 10 = 1
So 205110-48-1 is a valid CAS Registry Number.
InChI:InChI=1/C42H59N3O10/c1-11-32-42(8)36(44-40(50)55-42)25(4)33(46)23(2)21-41(7,51-18-14-15-28-20-29-16-12-13-17-30(29)43-22-28)37(26(5)34(47)27(6)38(49)53-32)54-39-35(48)31(45(9)10)19-24(3)52-39/h12-17,20,22-27,31-32,35-37,39,48H,11,18-19,21H2,1-10H3,(H,44,50)/b15-14+/t23-,24-,25-,26+,27-,31+,32+,35-,36-,37-,39+,41-,42-/m1/s1

205110-48-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (1R,2R,4R,6R,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-2,4,6,8,10,14-hexamethyl-6-[(E)-3-quinolin-3-ylprop-2-enoxy]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone

1.2 Other means of identification

Product number -
Other names ABT 773

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:205110-48-1 SDS

205110-48-1Synthetic route

C40H72N2O13

C40H72N2O13

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium hydrogensulfite; formic acid / water; ethanol / 2.5 h / 86 °C
2.1: dmap / dichloromethane / 3 h / 20 °C
3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
3.2: 28 h / -40 - 20 °C / Inert atmosphere
4.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere
5.1: hydrogenchloride / water; ethanol / 22 h
6.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere
6.2: 1 h / 10 °C / Inert atmosphere
7.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
8.1: methanol / Reflux
View Scheme
acetic acid 2-[4-(5-acetoxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-7-allyloxy-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
198557-85-6

acetic acid 2-[4-(5-acetoxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-7-allyloxy-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
1.2: 28 h / -40 - 20 °C / Inert atmosphere
2.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere
3.1: hydrogenchloride / water; ethanol / 22 h
4.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere
4.2: 1 h / 10 °C / Inert atmosphere
5.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
6.1: methanol / Reflux
View Scheme
C48H75N3O15

C48H75N3O15

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere
2.1: hydrogenchloride / water; ethanol / 22 h
3.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere
3.2: 1 h / 10 °C / Inert atmosphere
4.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
5.1: methanol / Reflux
View Scheme
2',4
198557-87-8

2',4"-O-diacetyl-6-O-allyl-11,12-cyclocarbamate erythromycin A

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride / water; ethanol / 22 h
2.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere
2.2: 1 h / 10 °C / Inert atmosphere
3.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
4.1: methanol / Reflux
View Scheme
acetic acid 2-(11-allyloxy-4-ethyl-8-hydroxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
205110-77-6

acetic acid 2-(11-allyloxy-4-ethyl-8-hydroxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere
1.2: 1 h / 10 °C / Inert atmosphere
2.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
3.1: methanol / Reflux
View Scheme
acetic acid 2-(11-allyloxy-4-ethyl-3a,7,9,11,13,15-hexamethyl-2,6,8,14-tetraoxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
205110-78-7

acetic acid 2-(11-allyloxy-4-ethyl-3a,7,9,11,13,15-hexamethyl-2,6,8,14-tetraoxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
2: methanol / Reflux
View Scheme
C44H61N3O11

C44H61N3O11

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
With methanol Reflux;32.95 g
6-O-allylerythromycin A
198482-51-8

6-O-allylerythromycin A

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dmap / dichloromethane / 3 h / 20 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
2.2: 28 h / -40 - 20 °C / Inert atmosphere
3.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere
4.1: hydrogenchloride / water; ethanol / 22 h
5.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere
5.2: 1 h / 10 °C / Inert atmosphere
6.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
7.1: methanol / Reflux
View Scheme
C55H104N2O14Si2

C55H104N2O14Si2

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: acetic acid / acetonitrile; water / 20 °C
2.1: sodium hydrogensulfite; formic acid / water; ethanol / 2.5 h / 86 °C
3.1: dmap / dichloromethane / 3 h / 20 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
4.2: 28 h / -40 - 20 °C / Inert atmosphere
5.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere
6.1: hydrogenchloride / water; ethanol / 22 h
7.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere
7.2: 1 h / 10 °C / Inert atmosphere
8.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
9.1: methanol / Reflux
View Scheme
2',4

2',4"-bis-O-trimethylsilylerythromycin A 9-O-(1-isopropoxycyclohexyl)oxime

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: potassium tert-butylate / dimethyl sulfoxide; tetrahydrofuran / 4 h / 0 °C
2.1: acetic acid / acetonitrile; water / 20 °C
3.1: sodium hydrogensulfite; formic acid / water; ethanol / 2.5 h / 86 °C
4.1: dmap / dichloromethane / 3 h / 20 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
5.2: 28 h / -40 - 20 °C / Inert atmosphere
6.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere
7.1: hydrogenchloride / water; ethanol / 22 h
8.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere
8.2: 1 h / 10 °C / Inert atmosphere
9.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere
10.1: methanol / Reflux
View Scheme
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(2-quinolin-3-yl-cyclopropylmethoxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(2-quinolin-3-yl-cyclopropylmethoxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
With palladium diacetate In diethyl ether; dichloromethane at 0℃; for 1.33h; Inert atmosphere;100 mg
propionic acid anhydride
123-62-6

propionic acid anhydride

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

C45H63N3O11

C45H63N3O11

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h;
ethyl 3-(chloroformyl)propionate
14794-31-1

ethyl 3-(chloroformyl)propionate

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

C48H67N3O13

C48H67N3O13

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 24h;110 mg
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
205110-48-1

10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

(3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-10-((2S,3R,4S,6R)-4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-propoxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

(3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-10-((2S,3R,4S,6R)-4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-propoxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate under 760.051 Torr; for 22h;175 mg

205110-48-1Downstream Products

205110-48-1Relevant articles and documents

6-O-SUBSTITUTED KETOLIDES HAVING ANTIBACTERIAL ACTIVITY

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, (2016/10/27)

PROBLEM TO BE SOLVED: To provide 6-O-substituted ketolides with antibacterial activity, having acid stability and enhanced activity toward gram negative bacteria and macrolide resistant gram positive bacteria. SOLUTION: This invention provides 6-O-substituted erythromycin ketolide derivatives such as formula (II) and compositions comprising the compounds. [Y and Z together form a group X; X is ketone, hydroxyimino or the like; or, one of Y and Z is H and the other is hydrogen, hydroxy or the like; Ra is H, hydroxy; Rc is H or a hydroxy protective group; R is a substituted methyl group]. COPYRIGHT: (C)2015,JPOandINPIT

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