Product Name

  • Name

    Telithromycin

  • EINECS 682-750-4
  • CAS No. 191114-48-4
  • Article Data8
  • CAS DataBase
  • Density 1.26 g/cm3
  • Solubility Sparingly soluble in water
  • Melting Point 176-188 °C
  • Formula C43H65N5O10
  • Boiling Point 966.2 °C at 760 mmHg
  • Molecular Weight 812.017
  • Flash Point 538.2 °C
  • Transport Information
  • Appearance
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 191114-48-4 (Telithromycin)
  • Hazard Symbols IrritantXi
  • Synonyms Erythromycin,3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-L-ribo-hexopyranosyl)oxy]-11,12-dideoxy-6-O-methyl-3-oxo-12,11-[oxycarbonyl[[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]imino]]-;HMR 3647;Ketek;RU 66647;
  • PSA 171.85000
  • LogP 4.86710

Synthetic route

2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate

2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Stage #1: 2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water for 0.5h; Product distribution / selectivity;		90%
Stage #1: 2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane for 0.5h; Product distribution / selectivity;		90%
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Product distribution / selectivity;
With pyridine hydrochloride; dimethyl sulfoxide; cyclohexyl-dimethyl-aminopropylcarbodimide hydrochloride In dichloromethane at 20 - 30℃; for 6h; Product distribution / selectivity; Pfitzner-Moffatt Oxidation;
Stage #1: 2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate With N-chloro-succinimide; dimethylsulfide In dichloromethane at -25 - 0℃; for 2.5h; Corey-Kim Oxidation;
Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Product distribution / selectivity;
2',4"-di-O-bis(trimethylsilyl)-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-6-O-methylerythromycin A-11,12-cycliccarbamate
1001326-77-7

2',4"-di-O-bis(trimethylsilyl)-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-6-O-methylerythromycin A-11,12-cycliccarbamate

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
With methanol at 20℃; for 7h; Product distribution / selectivity; Heating / reflux;98.9%
10-(4-dimethylamino-6-methyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-[4-(4-pyridin-3-yl-imidazol-1-yl)-butyl]-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
306770-60-5

10-(4-dimethylamino-6-methyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-[4-(4-pyridin-3-yl-imidazol-1-yl)-butyl]-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
With methanol at 20℃; for 7h; Product distribution / selectivity; Heating / reflux;98.9%
C36H55N3O12

C36H55N3O12

4-[4-(3-pyridyl)imidazol-1-yl]butylamine
173838-63-6

4-[4-(3-pyridyl)imidazol-1-yl]butylamine

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
In methanol; water; acetonitrile at 23 - 65℃; for 38h;
2'-O-acetyl-3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribohexopyranosyl)oxy]-11,12-dideoxy-6-O-methyl-3-oxo-12,11-[oxycarbonyl[[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]imino]]erythromycin
306770-59-2

2'-O-acetyl-3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribohexopyranosyl)oxy]-11,12-dideoxy-6-O-methyl-3-oxo-12,11-[oxycarbonyl[[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]imino]]erythromycin

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
With methanol at 20℃; for 16h; Product distribution / selectivity;
With isopropyl alcohol at 20℃; for 24h; Product distribution / selectivity;
With sodium hydroxide; water In ethanol at 0℃;
2'-benzoyl-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate

2'-benzoyl-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
With methanol for 7h; Heating / reflux;
2'-O-acetyl-10,11-didehydro-11-deoxy-12-O-(1H-1-imidazoylcarbonyl)-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A
160145-83-5

2'-O-acetyl-10,11-didehydro-11-deoxy-12-O-(1H-1-imidazoylcarbonyl)-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A

4-[4-(3-pyridyl)imidazol-1-yl]butylamine
173838-63-6

4-[4-(3-pyridyl)imidazol-1-yl]butylamine

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
In water; acetonitrile at 60℃; Substitution;50%
2'-O-acetate-3-O-descladinosyl-3-keto-10,11-anhydro-12-O-imidazolylcarbonyl-6-O-methylerythromycin

2'-O-acetate-3-O-descladinosyl-3-keto-10,11-anhydro-12-O-imidazolylcarbonyl-6-O-methylerythromycin

4-[4-(3-pyridyl)imidazol-1-yl]butylamine
173838-63-6

4-[4-(3-pyridyl)imidazol-1-yl]butylamine

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
In water; acetonitrile at 50℃; for 24h;72%
3-(1H-imidazol-4-yl)pyridine
51746-85-1

3-(1H-imidazol-4-yl)pyridine

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaH / dimethylformamide
2: aq. NH2NH2 / ethanol
3: 50 percent / acetonitrile; H2O / 60 °C
View Scheme
4-(3-pyridyl)-1H-imidazol-1-butanamide phthalimide
173838-67-0

4-(3-pyridyl)-1H-imidazol-1-butanamide phthalimide

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NH2NH2 / ethanol
2: 50 percent / acetonitrile; H2O / 60 °C
View Scheme
(R)-3-hydroxy-2-methylpent-1-ene
125637-07-2

(R)-3-hydroxy-2-methylpent-1-ene

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C
2: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h
3: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
4: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
5: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
6: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
7: 130 °C
8: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
9: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 9 steps
1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C
2: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h
3: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
4: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
5: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
6: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
7: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
8: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
9: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
(R)-tert-butyldimethyl((2-methylpent-1-en-3-yl)oxy)silane
135393-98-5

(R)-tert-butyldimethyl((2-methylpent-1-en-3-yl)oxy)silane

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h
2: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
3: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
4: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
6: 130 °C
7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
8: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 8 steps
1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h
2: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
3: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
4: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
6: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
8: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
(R)-3-((tert-butyldimethylsilyl)oxy)pentan-2-one
220018-22-4

(R)-3-((tert-butyldimethylsilyl)oxy)pentan-2-one

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
2: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
3: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
5: 130 °C
6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
7: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 7 steps
1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
2: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
3: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
5: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
7: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-2,4-dimethylpentanal

(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-2,4-dimethylpentanal

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
1.2: 12 h / -78 °C
2.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
3.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
5.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
6.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
8.1: 130 °C
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
10.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 10 steps
1.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
1.2: 12 h / -78 °C
2.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
3.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
5.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
6.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
8.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
10.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
C41H75NO12Si

C41H75NO12Si

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
3: 130 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
5: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 5 steps
1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
3: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
5: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
C41H73NO12Si

C41H73NO12Si

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
2: 130 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
4: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
2: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
4: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
C35H59NO12

C35H59NO12

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
3: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 3 steps
1: 130 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
3: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
6-((2R,3R,4R,6R)-7-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-4-methoxy-4,6-dimethylheptan-2-yl)-2,2,5-trimethyl-4H-1,3-dioxin-4-one

6-((2R,3R,4R,6R)-7-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-4-methoxy-4,6-dimethylheptan-2-yl)-2,2,5-trimethyl-4H-1,3-dioxin-4-one

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
2: hydrogen fluoride / acetonitrile / 12 h / 20 °C
3: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
4: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
5: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
6: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
7: 130 °C
8: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
9: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 9 steps
1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
2: hydrogen fluoride / acetonitrile / 12 h / 20 °C
3: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
4: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
5: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
6: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
7: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
8: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
9: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
C43H65NO10Si

C43H65NO10Si

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
2: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
3: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
4: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
6: 130 °C
7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
8: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 8 steps
1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
2: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
3: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
4: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
6: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
8: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
C27H47NO10

C27H47NO10

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
2: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
3: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
5: 130 °C
6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
7: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 7 steps
1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
2: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
3: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
5: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
7: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
(2S,3R,4S,6R)-4-(dimethylamino)-2-(((2R,3R,4R,6R)-4-methoxy-4,6-dimethyl-7-oxo-2-(2,2,5-trimethyl-4-oxo-4H-1,3-dioxin-6-yl)heptan-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl methyl carbonate

(2S,3R,4S,6R)-4-(dimethylamino)-2-(((2R,3R,4R,6R)-4-methoxy-4,6-dimethyl-7-oxo-2-(2,2,5-trimethyl-4-oxo-4H-1,3-dioxin-6-yl)heptan-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl methyl carbonate

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
2: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
4: 130 °C
5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
6: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 6 steps
1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
2: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
4: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
6: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
tert-butyl 2-methyl-3-oxopentanoate
26735-86-4

tert-butyl 2-methyl-3-oxopentanoate

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: acetic anhydride; sulfuric acid / 5 h / 0 - 20 °C
2.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -78 - 0 °C
2.2: 3 h / -78 - 20 °C
3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
3.2: 12 h / -78 °C
4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
10.1: 130 °C
11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
12.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 12 steps
1.1: acetic anhydride; sulfuric acid / 5 h / 0 - 20 °C
2.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -78 - 0 °C
2.2: 3 h / -78 - 20 °C
3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
3.2: 12 h / -78 °C
4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
10.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
12.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylpentan-2-ol

(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylpentan-2-ol

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: potassium hydride / diethyl ether; mineral oil / 1 h / 0 °C
1.2: 2 h / 20 °C
2.1: periodic acid / ethyl acetate
3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
3.2: 12 h / -78 °C
4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
10.1: 130 °C
11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
12.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 12 steps
1.1: potassium hydride / diethyl ether; mineral oil / 1 h / 0 °C
1.2: 2 h / 20 °C
2.1: periodic acid / ethyl acetate
3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
3.2: 12 h / -78 °C
4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
10.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
12.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
6-ethyl-2,2,5-trimethyl-4H-1,3-dioxin-4-one
135425-66-0

6-ethyl-2,2,5-trimethyl-4H-1,3-dioxin-4-one

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -78 - 0 °C
1.2: 3 h / -78 - 20 °C
2.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
2.2: 12 h / -78 °C
3.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
4.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
6.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
7.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
9.1: 130 °C
10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
11.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 11 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -78 - 0 °C
1.2: 3 h / -78 - 20 °C
2.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
2.2: 12 h / -78 °C
3.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
4.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
6.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
7.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
9.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
11.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
(Z)-((4-ethylidene-2,2,5-trimethyl-4H-1,3-dioxin-6-yl)oxy)trimethylsilane

(Z)-((4-ethylidene-2,2,5-trimethyl-4H-1,3-dioxin-6-yl)oxy)trimethylsilane

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
1.2: 12 h / -78 °C
2.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
3.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
5.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
6.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
8.1: 130 °C
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
10.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 10 steps
1.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
1.2: 12 h / -78 °C
2.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
3.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
5.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
6.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
8.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
10.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
(4S,5R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylhept-2-yn-4-ol

(4S,5R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylhept-2-yn-4-ol

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
2: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
4: 130 °C
5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
6: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 6 steps
1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
2: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
4: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
6: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
tert-butyl(((2R,4R)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methoxy-2-methylpentyl)oxy)diphenylsilane

tert-butyl(((2R,4R)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methoxy-2-methylpentyl)oxy)diphenylsilane

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: periodic acid / ethyl acetate
2.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
2.2: 12 h / -78 °C
3.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
4.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
6.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
7.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
9.1: 130 °C
10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
11.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
Multi-step reaction with 11 steps
1.1: periodic acid / ethyl acetate
2.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
2.2: 12 h / -78 °C
3.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
4.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
6.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
7.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
9.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -15 °C
11.1: acetonitrile; water; methanol / 38 h / 23 - 65 °C
View Scheme
2',4''-di-O-acetyl-6-O-methylerythromycin A
152235-55-7

2',4''-di-O-acetyl-6-O-methylerythromycin A

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / dichloromethane / 8.5 h / -5 - 20 °C
2: water; hydrogenchloride / ethanol / 6 h / 20 °C
3: phosphorus pentoxide; dimethyl sulfoxide / dichloromethane / 4 h / 20 °C
4: sodium hexamethyldisilazane / tetrahydrofuran / 4 h / 0 - 20 °C
5: water; acetonitrile / 24 h / 50 °C
View Scheme
clarithromycin
81103-11-9

clarithromycin

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: dichloromethane / 6 h / 20 °C
2: pyridine / dichloromethane / 8.5 h / -5 - 20 °C
3: water; hydrogenchloride / ethanol / 6 h / 20 °C
4: phosphorus pentoxide; dimethyl sulfoxide / dichloromethane / 4 h / 20 °C
5: sodium hexamethyldisilazane / tetrahydrofuran / 4 h / 0 - 20 °C
6: water; acetonitrile / 24 h / 50 °C
View Scheme
2',4''-di-O-acetyl-11,12-carbonate-6-O-methylerythromycin

2',4''-di-O-acetyl-11,12-carbonate-6-O-methylerythromycin

telithromycin
191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: water; hydrogenchloride / ethanol / 6 h / 20 °C
2: phosphorus pentoxide; dimethyl sulfoxide / dichloromethane / 4 h / 20 °C
3: sodium hexamethyldisilazane / tetrahydrofuran / 4 h / 0 - 20 °C
4: water; acetonitrile / 24 h / 50 °C
View Scheme
telithromycin
191114-48-4

telithromycin

3’-N-desmethyltelithromycin
255918-52-6

3’-N-desmethyltelithromycin

Conditions
ConditionsYield
With N-iodo-succinimide In acetonitrile at 0 - 20℃;68%
Stage #1: telithromycin With N-iodo-succinimide In acetonitrile at 0 - 20℃;
Stage #2: With water; sodium thiosulfate In acetonitrile		68%
With N-iodo-succinimide In acetonitrile at 0 - 20℃; Inert atmosphere;68%
With N-iodo-succinimide In acetonitrile
telithromycin
191114-48-4

telithromycin

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-OH-3-oxo-erythronolide A 11,12-carbamate

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-OH-3-oxo-erythronolide A 11,12-carbamate

Conditions
ConditionsYield
Stage #1: telithromycin With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; Swern oxidation;
Stage #2: With methanol; silica gel at 65℃;		55%
Stage #1: telithromycin With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -50℃; for 0.5h;
Stage #2: With triethylamine In dichloromethane at -50 - 20℃;
Stage #3: With methanol at 20℃;		44%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

telithromycin
191114-48-4

telithromycin

C44H67N5O12S
957065-70-2

C44H67N5O12S

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 20℃; for 5h;
telithromycin
191114-48-4

telithromycin

C43H65N5O9
1384954-33-9

C43H65N5O9

Conditions
ConditionsYield
Stage #1: telithromycin With 1,1'-Thiocarbonyldiimidazole at 20℃;
Stage #2: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride
telithromycin
191114-48-4

telithromycin

C46H71N5O10
1384954-36-2

C46H71N5O10

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-iodo-succinimide / acetonitrile
2: sodium cyanoborohydride
View Scheme
telithromycin
191114-48-4

telithromycin

C46H71N5O9
1384954-35-1

C46H71N5O9

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-iodo-succinimide / acetonitrile
2: sodium cyanoborohydride
3: 1,1'-Thiocarbonyldiimidazole / 20 °C
View Scheme
telithromycin
191114-48-4

telithromycin

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-O-(N-t-butylcarbonate-N,O-isopropylidene isoserinate)-3-oxo-erythronolide A 11,12-carbamate

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-O-(N-t-butylcarbonate-N,O-isopropylidene isoserinate)-3-oxo-erythronolide A 11,12-carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -50 °C
1.2: -50 - 20 °C
1.3: 20 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane
View Scheme
telithromycin
191114-48-4

telithromycin

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-O-isoserinate-3-erythronolide A 11,12-carbamate

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-O-isoserinate-3-erythronolide A 11,12-carbamate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -50 °C
1.2: -50 - 20 °C
1.3: 20 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane
3.1: trifluoroacetic acid; water / 1 h / 0 °C
4.1: trifluoroacetic acid; dimethylsulfide / 1 h / 0 °C
View Scheme
telithromycin
191114-48-4

telithromycin

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-O-(N-dimethylisoserinate)-3-oxo-erythronolide A 11,12-carbamate

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-O-(N-dimethylisoserinate)-3-oxo-erythronolide A 11,12-carbamate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -50 °C
1.2: -50 - 20 °C
1.3: 20 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane
3.1: trifluoroacetic acid; water / 1 h / 0 °C
4.1: trifluoroacetic acid; dimethylsulfide / 1 h / 0 °C
5.1: sodium tris(acetoxy)borohydride / tetrahydrofuran; water / 1 h
View Scheme
telithromycin
191114-48-4

telithromycin

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-O-allyl-3-oxo-erythronolide A 11,12-carbamate

11-N-[4-(4-pyridin-3-yl-imidazol-1-yl)butyl]-6-O-methyl-5-O-allyl-3-oxo-erythronolide A 11,12-carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -50 °C
1.2: -50 - 20 °C
1.3: 20 °C
2.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 24 h / Inert atmosphere; Reflux
View Scheme
telithromycin
191114-48-4

telithromycin

C43H63N5O12

C43H63N5O12

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -50 °C
1.2: -50 - 20 °C
1.3: 20 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane
3.1: trifluoroacetic acid; water / 1 h / 0 °C
View Scheme

Telithromycin History

French pharmaceutical company Hoechst Marion Roussel (later Sanofi-Aventis) began phase II/III clinical trials of telithromycin (HMR-3647) in 1998. Telithromycin was approved by the European Commission in July 2001 and subsequently went on sale in October 2001. In the US, telithromycin received FDA approval on April 1, 2004 .

Telithromycin Specification

The Telithromycin is an organic compound with the formula C43H65N5O10. The IUPAC name of this chemical is (1R,2S,4R,6R,7R,8R,10S,13S,14S)-7-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-6-methoxy-2,4,6,8,10,14-hexamethyl-17-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone. With the CAS registry number 191114-48-4, it is also named as 2H-oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)-tetrone, 4-ethyloctahydro-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]-10-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, (3aS,4S,7R,9R,10R,11S,13R,15S,15aR)-. The product's classification codes are Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Antimicrobial. Besides, it is the first ketolide antibiotic to enter clinical use. It is used to treat mild to moderate respiratory infections.

Physical properties about Telithromycin are: (1)ACD/LogP: 3.58; (2)# of Rule of 5 Violations: 2; (3)#H bond acceptors: 15; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 12; (6)Polar Surface Area: 160.85 Å2; (7)Index of Refraction: 1.588; (8)Molar Refractivity: 216.19 cm3; (9)Molar Volume: 641.7 cm3; (10)Polarizability: 85.7×10-24cm3; (11)Surface Tension: 44 dyne/cm; (12)Density: 1.26 g/cm3; (13)Flash Point: 538.2 °C; (14)Enthalpy of Vaporization: 147.43 kJ/mol; (15)Boiling Point: 966.2 °C at 760 mmHg.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2[C@@H]([C@@H](O[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C)[C@](OC)(C)C[C@H](C(=O)[C@@H](C)[C@H]3N(C(=O)O[C@]3(C)[C@@H](OC(=O)[C@@H]2C)CC)CCCCn4cc(nc4)c5cccnc5)C)C
(2)InChI: InChI=1/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27-,28+,29-,32+,33+,36-,37-,38-,40+,42+,43-/m1/s1
(3)InChIKey: LJVAJPDWBABPEJ-WIFJXVANBD
(4)Std. InChI: InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27-,28+,29-,32+,33+,36-,37-,38-,40+,42+,43-/m1/s1
(5)Std. InChIKey: LJVAJPDWBABPEJ-WIFJXVANSA-N

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View