CAS No.191114-48-4,Telithromycin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	191114-48-4
Name:	Telithromycin
Article Data:	8

Formula:	C₄₃H₆₅N₅O₁₀
Molecular Weight:	812.017
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;
EINECS:	682-750-4
Density:	1.26 g/cm³
Melting Point:	176-188 °C
Boiling Point:	966.2 °C at 760 mmHg
Flash Point:	538.2 °C
Solubility:	Sparingly soluble in water
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
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

: 191114-48-4
telithromycin

Conditions

Conditions	Yield
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;

: 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

: 191114-48-4
telithromycin

Conditions

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

: 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

: 191114-48-4
telithromycin

Conditions

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

: C36H55N3O12

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

: 191114-48-4
telithromycin

Conditions

Conditions	Yield
In methanol; water; acetonitrile at 23 - 65℃; for 38h;

: 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

: 191114-48-4
telithromycin

Conditions

Conditions	Yield
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

: 191114-48-4
telithromycin

Conditions

Conditions	Yield
With methanol for 7h; Heating / reflux;

: 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

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

: 191114-48-4
telithromycin

Conditions

Conditions	Yield
In water; acetonitrile at 60℃; Substitution;	50%

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

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

: 191114-48-4
telithromycin

Conditions

Conditions	Yield
In water; acetonitrile at 50℃; for 24h;	72%

: 51746-85-1
3-(1H-imidazol-4-yl)pyridine

: 191114-48-4
telithromycin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH / dimethylformamide 2: aq. NH2NH2 / ethanol 3: 50 percent / acetonitrile; H2O / 60 °C View Scheme

: 173838-67-0
4-(3-pyridyl)-1H-imidazol-1-butanamide phthalimide

: 191114-48-4
telithromycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NH2NH2 / ethanol 2: 50 percent / acetonitrile; H2O / 60 °C View Scheme

Raw Materials

Total:95 Page 1 of 3 1 2 3 Next>>

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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 .

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