9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
With potassium borohydride In methanol at 0 - 5℃; for 2h; | 93% |
Stage #1: 9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A With hydrogen; acetic acid; platinum(IV) oxide In methanol at 40 - 45℃; pH=5 - 6; Stage #2: With sodium hydroxide In water pH=11 - 12; | 85% |
Stage #1: 9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A With sodium tetrahydroborate; acetic acid pH=6 - 8; Heating; Stage #2: With gluconic acid at 8℃; Reagent/catalyst; Temperature; | 84.4% |
With sodium tetrahydroborate In methanol at 0 - 25℃; Inert atmosphere; | 77% |
With methanol; sodium tetrahydroborate at 0 - 20℃; for 24h; | 70.3% |
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: C37H66N2O12 With perchloric acid; hydrogen; platinum on activated charcoal In methanol at 5 - 42℃; under 10298 Torr; for 3h; pH=5.5; Stage #2: With sodium hydroxide In water pH=12 - 12.5; | 91.5% |
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: C37H66N2O12 With perchloric acid; hydrogen; platinum on activated charcoal In methanol; water at 5 - 42℃; under 10298 Torr; for 3h; pH=5.5; Stage #2: With sodium hydroxide In water pH=12 - 12.5; Product distribution / selectivity; | 86.6% |
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: C37H66N2O12 With potassium borohydride; acetic acid In water at 14℃; under 22502.3 Torr; pH=7; Flow reactor; Stage #2: In ethyl acetate Stage #3: With hydrogenchloride In water; ethyl acetate for 0.05h; Pressure; Temperature; pH-value; Solvent; | 86% |
(9-E)-deoxo-9-hydroximinoerythromycin A
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: (9-E)-deoxo-9-hydroximinoerythromycin A With calcium(II) bis(trifluoromethanesulfonyl)imide; tert-butylammonium hexafluorophosphate(V) In 1,2-dimethoxyethane; 1,2-dichloro-ethane at 80℃; for 5h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 51h; | 78% |
Multi-step reaction with 2 steps 1: p-toluenesulfonyl chloride; sodium hydrogencarbonate / acetone; water / 4 h / 0 - 20 °C 2: sodium tetrahydroborate; methanol / 24 h / 0 - 20 °C View Scheme |
erythromycin A 9-(E)-oxime
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Rearrangement; Beckmann-like rearrangement; reduction; | 45% |
Stage #1: erythromycin A 9-(E)-oxime With sodium hydrogencarbonate; p-toluenesulfonyl chloride In acetone Beckmann rearrangement; Stage #2: With hydrogen; platinum on activated charcoal In methanol under 30003 Torr; for 12h; Further stages.; | |
Multi-step reaction with 2 steps 1: methanol; water / 5 h / 5 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 4 - 20 °C / Inert atmosphere View Scheme |
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
With platinum on carbon; hydrogen In methanol at 40 - 45℃; under 7500.75 Torr; for 4h; Autoclave; | 17.1% |
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
With Amberlite IRA-743; sulfuric acid; water for 0.5h; pH=2.8; |
C38H70N2O12
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: C38H70N2O12 With sodium tetrahydroborate; formic acid In water at 0 - 20℃; for 11h; pH=6 - 8; Stage #2: With malic acid In water Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages; |
C44H74N2O15S
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 4 - 20℃; Beckmann rearrangement; Inert atmosphere; | 300 mg |
erythromycin
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydroxylamine; acetic acid / water; isopropyl alcohol / 15 h / 50 °C / Inert atmosphere 2: methanol; water / 5 h / 5 °C / Inert atmosphere 3: sodium tetrahydroborate / methanol / 4 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; triethylamine / methanol / 24 h / Reflux 2: p-toluenesulfonyl chloride; sodium hydrogencarbonate / acetone; water / 4 h / 0 - 20 °C 3: sodium tetrahydroborate; methanol / 24 h / 0 - 20 °C View Scheme |
erythromycin A oxime thiocyanate
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: erythromycin A oxime thiocyanate With sodium hydroxide In dichloromethane at 10℃; pH=9 - 11; Stage #2: With sodium tetrahydroborate In dichloromethane at 10℃; pH=0.5 - 2.5; | 57.4 g |
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; p-toluenesulfonyl chloride / acetone / 4 h / 0 - 10 °C 2.1: phosphoric acid; potassium borohydride / water / 8 h / 0 - 5 °C / pH 7 - 9 2.2: 3 h / 0 - 5 °C / pH 2.5 - 3 View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydroxide / dichloromethane; water / 38 °C 2.1: sodium carbonate; p-toluenesulfonyl chloride / water / 3.2 h / 12 °C / pH Ca. 7 3.1: acetic acid; potassium borohydride / water / 14 °C / 22502.3 Torr / pH 7 / Flow reactor 3.3: 0.05 h View Scheme |
erythromycin A thiocyanate
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; triethylamine / methanol / 52 h / 30 - 55 °C / pH 6.3 - 6.7 2.1: sodium hydrogencarbonate; p-toluenesulfonyl chloride / acetone / 4 h / 0 - 10 °C 3.1: phosphoric acid; potassium borohydride / water / 8 h / 0 - 5 °C / pH 7 - 9 3.2: 3 h / 0 - 5 °C / pH 2.5 - 3 View Scheme |
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: erythromycin A 6,9-imino ether With potassium borohydride; phosphoric acid In water at 0 - 5℃; for 8h; pH=7 - 9; Stage #2: With hydrogenchloride In dichloromethane; water at 0 - 5℃; for 3h; pH=2.5 - 3; Reagent/catalyst; |
benzyl chloroformate
9-Deoxo-9a-aza-9a-homoerythromycin A
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-2-O-[(phenylmethoxy)carbonyl]-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one
Conditions | Yield |
---|---|
In dichloromethane at 0℃; | 100% |
Stage #1: benzyl chloroformate; 9-Deoxo-9a-aza-9a-homoerythromycin A In dichloromethane at -10 - 3℃; for 0.166667h; Stage #2: With triethylamine In dichloromethane at 3℃; for 2h; | 96.9% |
In dichloromethane at 0 - 5℃; for 1h; | 84.57% |
acrylonitrile
9-Deoxo-9a-aza-9a-homoerythromycin A
9-deoxo-9a-aza-9a-(β-cyanoethyl)-9a-homoerythromycin A
Conditions | Yield |
---|---|
at 80℃; for 24h; Michael addition; | 99% |
at 60℃; for 16h; Inert atmosphere; | 63% |
for 7h; Heating / reflux; | 41% |
formaldehyd
9-Deoxo-9a-aza-9a-homoerythromycin A
Zithromax(R)
Conditions | Yield |
---|---|
With formic acid In acetone at 30 - 55℃; for 4h; | 95% |
Stage #1: formaldehyd; 9-Deoxo-9a-aza-9a-homoerythromycin A With formic acid In acetone at 40 - 45℃; for 7 - 8h; Stage #2: With sodium hydroxide In water; acetone pH=11 - 11.5; | 87% |
With formic acid In water; ethyl acetate for 2h; Heating / reflux; | 77% |
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
With dihydrogen peroxide In methanol; water at 0 - 20℃; for 2h; | 94.3% |
With dihydrogen peroxide In methanol; water at 0 - 20℃; for 2h; | 94.3% |
Benzyl isothiocyanate
9-Deoxo-9a-aza-9a-homoerythromycin A
C45H77N3O12S
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 60℃; for 3h; | 92% |
Conditions | Yield |
---|---|
In dichloromethane at -5 - 0℃; for 3h; | 92% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; 9-Deoxo-9a-aza-9a-homoerythromycin A With formic acid In acetone at 40 - 45℃; for 7 - 8h; Stage #2: With sodium hydroxide In water; acetone pH=11 - 11.5; Stage #3: With water In acetone at 20℃; for 24h; | 87% |
Stage #1: formaldehyd; 9-Deoxo-9a-aza-9a-homoerythromycin A With formic acid In water; acetone at 20 - 55℃; for 8h; Stage #2: With water In acetone at 38 - 40℃; for 10 - 12h; Stage #3: With water | 76.7% |
Stage #1: formaldehyd; 9-Deoxo-9a-aza-9a-homoerythromycin A With formic acid In chloroform; water at 20 - 55℃; for 10 - 20h; Heating / reflux; Stage #2: With water In acetone at 38 - 40℃; for 10 - 12h; | 73% |
di-tert-butyl dicarbonate
9-Deoxo-9a-aza-9a-homoerythromycin A
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-((2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-2-O-(tert-butoxycarbonyl)-β-D-xylo-hexopyranosyl)oxy)-1-oxa-6-(tert-butoxycarbonyl)azacyclopentadecan-15-one
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran at -5 - 5℃; for 10.5h; Solvent; Reflux; | 86.3% |
acrylic acid methyl ester
9-Deoxo-9a-aza-9a-homoerythromycin A
9-deoxo-9a-aza-9a-(γ-hydroxypropyl)-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: acrylic acid methyl ester; 9-Deoxo-9a-aza-9a-homoerythromycin A at 60℃; for 30h; Addition; hetero-Michael addition; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Reduction; | 84% |
9-Deoxo-9a-aza-9a-homoerythromycin A
3-O-decladinosyl-9-deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; for 24h; pH=1; | 79% |
Stage #1: 9-Deoxo-9a-aza-9a-homoerythromycin A With formaldehyd; formic acid In water for 30h; Reflux; Stage #2: With sodium hydroxide In water pH=11; | 61% |
With hydrogenchloride at 20℃; for 12h; |
acrylic acid methyl ester
9-Deoxo-9a-aza-9a-homoerythromycin A
3-(9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A) propionic acid methyl ester
Conditions | Yield |
---|---|
In chloroform at 60℃; for 48h; | 65% |
In chloroform at 60℃; for 48h; Heating / reflux; | 53.7% |
9-Deoxo-9a-aza-9a-homoerythromycin A
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10,11,13-pentahydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadecan-15-one
Conditions | Yield |
---|---|
With hydrogenchloride In water at 50℃; for 10h; | 60.1% |
With hydrogenchloride In water at 60℃; for 64h; |
imidazole-1-carboxylic acid [2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-amide
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: imidazole-1-carboxylic acid [2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-amide; 9-Deoxo-9a-aza-9a-homoerythromycin A In N,N-dimethyl-formamide; acetonitrile at 50℃; for 2h; Acylation; Stage #2: With pyridine; hydrogen fluoride In tetrahydrofuran at 0℃; Decomposition; | 50% |
(11-carboxyundecyl)triphenylphosphonium bromide
9-Deoxo-9a-aza-9a-homoerythromycin A
{11-[(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-azacyclopentadecan-6-yl]-11-oxoundecyl}triphenylphosphonium chloride
Conditions | Yield |
---|---|
Stage #1: (11-carboxyundecyl)triphenylphosphonium bromide With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 40℃; for 0.5h; Stage #2: 9-Deoxo-9a-aza-9a-homoerythromycin A In dichloromethane at 40℃; Stage #3: In methanol | 49% |
Stage #1: (11-carboxyundecyl)triphenylphosphonium bromide With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 40℃; for 0.5h; Stage #2: 9-Deoxo-9a-aza-9a-homoerythromycin A In dichloromethane at 40℃; Stage #3: In methanol | 0.4 g |
Conditions | Yield |
---|---|
In toluene at 20℃; for 1h; Inert atmosphere; | 47% |
3-methoxybiphenyl-4-yl isothiocyanate
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 60℃; | 41% |
isopropyl isothiocyanate
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 60℃; | 39% |
benzyl isothiocyanate
9-Deoxo-9a-aza-9a-homoerythromycin A
C45H77N3O13
Conditions | Yield |
---|---|
In toluene Inert atmosphere; | 35% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); triethylamine at 20 - 80℃; for 22h; Inert atmosphere; | 26% |
propionaldehyde
9-Deoxo-9a-aza-9a-homoerythromycin A
n-propyl azithromycin
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 70℃; for 7h; Inert atmosphere; | 24% |
With 5%-palladium/activated carbon; hydrogen In ethanol at 35 - 45℃; under 750.075 - 4500.45 Torr; for 4h; Temperature; Pressure; Solvent; Reagent/catalyst; Autoclave; |
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide Inert atmosphere; | 21% |
9-Deoxo-9a-aza-9a-homoerythromycin A
cyclohexanecarbaldehyde
C44H82N2O12
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide Inert atmosphere; | 21% |
4-Ethynylbenzaldehyde
9-Deoxo-9a-aza-9a-homoerythromycin A
Conditions | Yield |
---|---|
Stage #1: 4-Ethynylbenzaldehyde; 9-Deoxo-9a-aza-9a-homoerythromycin A With acetic acid In N,N-dimethyl-formamide for 0.5h; Stage #2: With sodium cyanoborohydride In N,N-dimethyl-formamide at 70℃; for 7h; | 20% |
The CAS register number of Azathramycin is 76801-85-9. It also can be called as 9-Deoxo-9a-aza-9a-homoerythromycin A and the systematic name about this chemical is 2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methylhexopyranoside. The molecular formula about this chemical is C37H70N2O12 and molecular weight is 734.96. It belongs to the following product categories which include Intermediates & Fine Chemicals; Pharmaceuticals and so on.
Physical properties about Azathramycin are: (1)ACD/LogP: 3.11; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 7.4): 0.11; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1.16; (8)#H bond acceptors: 14; (9)#H bond donors: 6; (10)#Freely Rotating Bonds: 12; (11)Polar Surface Area: 188.87Å2; (12)Index of Refraction: 1.536; (13)Molar Refractivity: 192.7 cm3; (14)Molar Volume: 617.8 cm3; (15)Polarizability: 76.39x10-24cm3; (16)Surface Tension: 50.7 dyne/cm; (17)Flash Point: 446.8 °C; (18)Enthalpy of Vaporization: 134.9 kJ/mol; (19)Boiling Point: 815.2 °C at 760 mmHg; (20)Vapour Pressure: 8.8E-31 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: CN(C)C3CC(C)OC(OC2C(C)C(OC1CC(C)(OC)C(O)C(C)O1)C(C)C(=O)OC(CC)C(C)(O)C(O)C(C)NCC(C)CC2(C)O)C3O
(2)InChI: InChI=1/C37H70N2O12/c1-14-26-37(10,45)30(41)23(6)38-18-19(2)16-35(8,44)32(51-34-28(40)25(39(11)12)15-20(3)47-34)21(4)29(22(5)33(43)49-26)50-27-17-36(9,46-13)31(42)24(7)48-27/h19-32,34,38,40-42,44-45H,14-18H2,1-13H3
(3)InChIKey: HRKNNHYKWGYTEN-UHFFFAOYAE
(4)Std. InChI: InChI=1S/C37H70N2O12/c1-14-26-37(10,45)30(41)23(6)38-18-19(2)16-35(8,44)32(51-34-28(40)25(39(11)12)15-20(3)47-34)21(4)29(22(5)33(43)49-26)50-27-17-36(9,46-13)31(42)24(7)48-27/h19-32,34,38,40-42,44-45H,14-18H2,1-13H3
(5)Std. InChIKey: HRKNNHYKWGYTEN-UHFFFAOYSA-N
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