Product Name

  • Name

    Azathramycin

  • EINECS 616-385-9
  • CAS No. 76801-85-9
  • Article Data21
  • CAS DataBase
  • Density 1.18 g/cm3
  • Solubility
  • Melting Point 126-136°C
  • Formula C37H70N2O12
  • Boiling Point 815.2 °C at 760 mmHg
  • Molecular Weight 734.969
  • Flash Point 446.8 °C
  • Transport Information
  • Appearance White solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 76801-85-9 (Azathramycin)
  • Hazard Symbols
  • Synonyms 1-Oxa-6-azacyclopentadecan-15-one,13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-b-D-xylo-hexopyranosyl]oxy]-,[2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*)]-;9-Deoxo-9a-aza-9a-homoerythromycin A;Azaerythromycin A;Azathramycin;
  • PSA 188.87000
  • LogP 1.88730

Synthetic route

9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A
342371-84-0

9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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%
C37H66N2O12

C37H66N2O12

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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%
C37H66N2O12

C37H66N2O12

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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%
C37H66N2O12

C37H66N2O12

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
111321-02-9

erythromycin A 9-(E)-oxime

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
erythromycin 6,9-imino ether

erythromycin 6,9-imino ether

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
With platinum on carbon; hydrogen In methanol at 40 - 45℃; under 7500.75 Torr; for 4h; Autoclave;17.1%
C70H128BN4O26(1-)*Na(1+)

C70H128BN4O26(1-)*Na(1+)

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
With Amberlite IRA-743; sulfuric acid; water for 0.5h; pH=2.8;
C38H70N2O12
944124-75-8

C38H70N2O12

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
227948-37-0

C44H74N2O15S

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 4 - 20℃; Beckmann rearrangement; Inert atmosphere;300 mg
erythromycin
114-07-8

erythromycin

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
1357466-70-6

erythromycin A oxime thiocyanate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
7704-67-8

erythromycin A thiocyanate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
erythromycin A 6,9-imino ether

erythromycin A 6,9-imino ether

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
501-53-1

benzyl chloroformate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

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
352032-78-1

(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
ConditionsYield
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
107-13-1

acrylonitrile

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

9-deoxo-9a-aza-9a-(β-cyanoethyl)-9a-homoerythromycin A
92627-70-8

9-deoxo-9a-aza-9a-(β-cyanoethyl)-9a-homoerythromycin A

Conditions
ConditionsYield
at 80℃; for 24h; Michael addition;99%
at 60℃; for 16h; Inert atmosphere;63%
for 7h; Heating / reflux;41%
formaldehyd
50-00-0

formaldehyd

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

9-deoxo-9-dihydro-3'-N-oxide-9a-aza-9a-homoerythromycin A

9-deoxo-9-dihydro-3'-N-oxide-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
622-78-6

Benzyl isothiocyanate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

C45H77N3O12S
166036-09-5

C45H77N3O12S

Conditions
ConditionsYield
With triethylamine In acetonitrile at 60℃; for 3h;92%
phenyl chloroformate
1885-14-9

phenyl chloroformate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

C44H74N2O14

C44H74N2O14

Conditions
ConditionsYield
In dichloromethane at -5 - 0℃; for 3h;92%
formaldehyd
50-00-0

formaldehyd

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

azithromycin dihydrate

azithromycin dihydrate

Conditions
ConditionsYield
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
24424-99-5

di-tert-butyl dicarbonate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

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

(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
ConditionsYield
With dmap In tetrahydrofuran at -5 - 5℃; for 10.5h; Solvent; Reflux;86.3%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

9-deoxo-9a-aza-9a-(γ-hydroxypropyl)-9a-homoerythromycin A
96779-85-0

9-deoxo-9a-aza-9a-(γ-hydroxypropyl)-9a-homoerythromycin A

Conditions
ConditionsYield
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
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

3-O-decladinosyl-9-deoxo-9a-aza-9a-homoerythromycin A
111247-94-0

3-O-decladinosyl-9-deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
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
292638-85-8

acrylic acid methyl ester

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

3-(9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A) propionic acid methyl ester
955955-02-9

3-(9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A) propionic acid methyl ester

Conditions
ConditionsYield
In chloroform at 60℃; for 48h;65%
In chloroform at 60℃; for 48h; Heating / reflux;53.7%
9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

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
111247-95-1

(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
ConditionsYield
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
287727-89-3

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
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

9a-aza-9a-[(3'-deoxythymidin-3'-yl)aminocarbonyl]-9-deoxo-9a-homoerythromycin A

9a-aza-9a-[(3'-deoxythymidin-3'-yl)aminocarbonyl]-9-deoxo-9a-homoerythromycin A

Conditions
ConditionsYield
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
7530-96-3

(11-carboxyundecyl)triphenylphosphonium bromide

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

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

{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
ConditionsYield
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
ethyl isocyanate
109-90-0

ethyl isocyanate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

C40H75N3O13
1289429-77-1

C40H75N3O13

Conditions
ConditionsYield
In toluene at 20℃; for 1h; Inert atmosphere;47%
3-methoxybiphenyl-4-yl isothiocyanate
1304028-65-6

3-methoxybiphenyl-4-yl isothiocyanate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

9a,11-O-{N'-[4-(3-methoxy)biphenyl]carbonimidoyl}-9-deoxo-9a-aza-9a-homoerythromycin A

9a,11-O-{N'-[4-(3-methoxy)biphenyl]carbonimidoyl}-9-deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
With triethylamine In acetonitrile at 60℃;41%
isopropyl isothiocyanate
2253-73-8

isopropyl isothiocyanate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

9a,11-O-(N'-isopropropylcarbonimidoyl)-9-deoxo-9a-aza-9a-homoerythromycin A

9a,11-O-(N'-isopropropylcarbonimidoyl)-9-deoxo-9a-aza-9a-homoerythromycin A

Conditions
ConditionsYield
With triethylamine In acetonitrile at 60℃;39%
benzyl isothiocyanate
3173-56-6

benzyl isothiocyanate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

C45H77N3O13
166036-08-4

C45H77N3O13

Conditions
ConditionsYield
In toluene Inert atmosphere;35%
Allyl acetate
591-87-7

Allyl acetate

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

C40H74N2O12
119471-59-9

C40H74N2O12

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine at 20 - 80℃; for 22h; Inert atmosphere;26%
propionaldehyde
123-38-6

propionaldehyde

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

n-propyl azithromycin
92594-48-4

n-propyl azithromycin

Conditions
ConditionsYield
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;
benzaldehyde
100-52-7

benzaldehyde

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

C44H76N2O12
119471-61-3

C44H76N2O12

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide Inert atmosphere;21%
9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

C44H82N2O12
1289430-07-4

C44H82N2O12

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide Inert atmosphere;21%
4-Ethynylbenzaldehyde
63697-96-1

4-Ethynylbenzaldehyde

9-Deoxo-9a-aza-9a-homoerythromycin A
76801-85-9

9-Deoxo-9a-aza-9a-homoerythromycin A

(N10-(4-ethynylbenzyl))azithromycin

(N10-(4-ethynylbenzyl))azithromycin

Conditions
ConditionsYield
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%

Azathramycin Specification

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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