76801-85-9

Basic information

• Product Name: Azathramycin
• Synonyms: DESMETHYL AZITHROMYCIN;AZAERYTHROMYCIN A (100 MG) (9-DEOXO-9A-AZA-9A-HOMOERYTHROMYCIN A);9-Deoxo-9a-aza-9a-homo Erythromycin A;Azaerythromycin A;Azathramycin;Desmethyl;10-dihydro-10-deoxo-11-azaerythromycin A;Desmethylazythromicin
• CAS NO: 76801-85-9
• Molecular Formula: C₃₇H₇₀N₂O₁₂
• Molecular Weight: 734.962
• EINECS: 1308068-626-2
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 76801-85-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 126-136°C
• Boiling Point: 815.2 °C at 760 mmHg
• Flash Point: 446.8 °C
• Appearance: White solid
• Density: 1.18
• Vapor Pressure: 8.8E-31mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 13.29±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Azathramycin(CAS DataBase Reference)
• NIST Chemistry Reference: Azathramycin(76801-85-9)
• EPA Substance Registry System: Azathramycin(76801-85-9)

Safety Data

• Hazardous Substances Data: 76801-85-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

9-Deoxo-9a-aza-9a-homo Erythromycin A (Azithromycin EP Impurity A) is a novel intermediate of Azithromycin that acts as antibiotic.

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

Synthetic route

9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A (342371-84-0) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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%

C37H66N2O12 → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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%

C37H66N2O12 → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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%

C37H66N2O12 → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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 (13127-18-9) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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 (111321-02-9) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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

erythromycin 6,9-imino ether → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

Conditions	Yield
With platinum on carbon; hydrogen In methanol at 40 - 45℃; under 7500.75 Torr; for 4h; Autoclave;	17.1%

C70H128BN4O26(1-)*Na(1+) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

Conditions	Yield
With Amberlite IRA-743; sulfuric acid; water for 0.5h; pH=2.8;

C38H70N2O12 (944124-75-8) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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 (227948-37-0) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

Conditions	Yield
With sodium tetrahydroborate In methanol at 4 - 20℃; Beckmann rearrangement; Inert atmosphere;	300 mg

erythromycin (114-07-8) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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 (1357466-70-6) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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 (7704-67-8) → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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

erythromycin A 6,9-imino ether → 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9)

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 (501-53-1) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → (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)

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 (107-13-1) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → 9-deoxo-9a-aza-9a-(β-cyanoethyl)-9a-homoerythromycin A (92627-70-8)

Conditions	Yield
at 80℃; for 24h; Michael addition;	99%
at 60℃; for 16h; Inert atmosphere;	63%
for 7h; Heating / reflux;	41%

formaldehyd (50-00-0) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → Zithromax(R) (83905-01-5, 92470-27-4)

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 (76801-85-9) → 9-deoxo-9-dihydro-3'-N-oxide-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 (622-78-6) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → C45H77N3O12S (166036-09-5)

Conditions	Yield
With triethylamine In acetonitrile at 60℃; for 3h;	92%

phenyl chloroformate (1885-14-9) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → C44H74N2O14

Conditions	Yield
In dichloromethane at -5 - 0℃; for 3h;	92%

formaldehyd (50-00-0) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → azithromycin dihydrate

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 (24424-99-5) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → (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 (292638-85-8) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → 9-deoxo-9a-aza-9a-(γ-hydroxypropyl)-9a-homoerythromycin A (96779-85-0)

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 (76801-85-9) → 3-O-decladinosyl-9-deoxo-9a-aza-9a-homoerythromycin A (111247-94-0)

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 (292638-85-8) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → 3-(9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A) propionic acid methyl ester (955955-02-9)

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 (76801-85-9) → (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)

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 (287727-89-3) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → 9a-aza-9a-[(3'-deoxythymidin-3'-yl)aminocarbonyl]-9-deoxo-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 (7530-96-3) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → {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

ethyl isocyanate (109-90-0) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → C40H75N3O13 (1289429-77-1)

Conditions	Yield
In toluene at 20℃; for 1h; Inert atmosphere;	47%

3-methoxybiphenyl-4-yl isothiocyanate (1304028-65-6) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → 9a,11-O-{N'-[4-(3-methoxy)biphenyl]carbonimidoyl}-9-deoxo-9a-aza-9a-homoerythromycin A

Conditions	Yield
With triethylamine In acetonitrile at 60℃;	41%

isopropyl isothiocyanate (2253-73-8) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → 9a,11-O-(N'-isopropropylcarbonimidoyl)-9-deoxo-9a-aza-9a-homoerythromycin A

Conditions	Yield
With triethylamine In acetonitrile at 60℃;	39%

benzyl isothiocyanate (3173-56-6) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → C45H77N3O13 (166036-08-4)

Conditions	Yield
In toluene Inert atmosphere;	35%

Allyl acetate (591-87-7) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → C40H74N2O12 (119471-59-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triethylamine at 20 - 80℃; for 22h; Inert atmosphere;	26%

propionaldehyde (123-38-6) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → n-propyl azithromycin (92594-48-4)

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;

benzaldehyde (100-52-7) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → C44H76N2O12 (119471-61-3)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide Inert atmosphere;	21%

9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) + cyclohexanecarbaldehyde (2043-61-0) → C44H82N2O12 (1289430-07-4)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide Inert atmosphere;	21%

4-Ethynylbenzaldehyde (63697-96-1) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → (N10-(4-ethynylbenzyl))azithromycin

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%

Upstream product

• 111321-02-9 erythromycin A 9-(E)-oxime 
• 7704-67-8 erythromycin thiocyanate A 
• 13127-18-9 (9-E)-deoxo-9-hydroximinoerythromycin A 
• 1357466-70-6 erythromycin A oxime thiocyanate 
• 114-07-8 erythromycin 
• 227948-37-0 C₄₄H₇₄N₂O₁₅S 
• 342371-84-0 9-deoxo-6-deoxy-6,9-epoxy-9,9a-didehydro-9a-aza-homoerythromycin A 
• 944124-75-8 C₃₈H₇₀N₂O₁₂ 
• 13127-18-9 erythromycin A oxime 
• 111247-90-6 C₄₅H₇₅N₃O₁₆S*ClH 
• 99290-97-8 C₃₇H₆₆N₂O₁₂ 

Downstream Products

• 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 
• 117772-70-0 azithromycin dihydrate 
• 1289430-02-9 C₄₅H₇₈N₂O₁₂ 
• 862203-04-1 C₄₄H₇₅FN₂O₁₂ 
• 119471-61-3 C₄₄H₇₆N₂O₁₂ 
• 166036-08-4 C₄₅H₇₇N₃O₁₃ 
• 1289430-07-4 C₄₄H₈₂N₂O₁₂ 
• 166036-09-5 C₄₅H₇₇N₃O₁₂S 
• 117772-70-0 azithromycin Monohydrate 
• 83905-01-5 Zithromax(R) 
• 217501-36-5 C₄₈H₇₈N₂O₁₄ 

Relevant articles and documents

Method for synthesizing azorithromycin by utilizing erythromycin thiocyanate oxime

The invention relates to a method for synthesizing azithromycin by utilizing erythromycin thiocyanate oxime. The method comprises the following process steps: removing thiocyanate radicals through erythromycin thiocyanate oxime dissociation, performing rearrangement reaction, performing continuous back extraction, performing continuous reduction reaction and separation, and performing azithromycin crystallizing. According to the invention, the thiocyanate radicals are removed before the rearrangement reaction and then the rearrangement is performed, the reduction reaction adopts a continuous reaction process, the reaction mode is changed, and the process is high in reaction efficiency, low in production cost, small in environmental pollution, high in product yield and good in product quality.

Novel crystal-form compound of dihydroerythromycin and preparation method thereof

The invention relates to a novel crystal-form compound of dihydroerythromycin and a preparation method thereof, and belongs to the technical field of synthesis of heterocyclic compounds. Erythromycinimide ether is dissolved in methanol, a catalyst Pt/C is added after acid adjustment, and a hydrogenation reaction is performed; after the reaction is finished, the catalyst is filtered, and a set amount of methanol is recovered; the temperature is dropped and the alkalinity is adjusted to the pH value of 10-12, a set amount of water is added drop by drop, and the novel crystal-form compound of dihydroerythromycin is obtained by filtration and drying. The preparation method is applied in synthesis of dihydroerythromycin and has the advantages of good fluidity, easy packaging, high liquid content and the like.

Preparation method of norazithromycin

The invention discloses a preparation method of norazithromycin and relates to the technical field of macrolide antibiotics. The preparation method comprises the following steps: reducing erythrocin A 6,9-imino ether in water at 0 DEG C to room temperature under the pH of 7.0-9.0 by using a reducing agent sodium borohydride or potassium borohydride; then in the presence of an organic solvent and water, performing continuous hydrolysis at 0 DEG C to room temperature under the pH of 2.0-3.0; then adding two-phase reaction liquids after continuous hydrolysis into an alkaline aqueous solution, adjusting the pH to be greater than or equal to 12, stirring, layering and abandoning the aqueous phase, wherein the organic solvent is dichloromethane, chloroform, 1,2-dichloromethane, ethyl acetate or butyl acetate; and after the last hydrolysis reaction in continuous hydrolysis, performing layering, directly adding the aqueous phase into the alkaline aqueous solution, adjusting the pH to be greater than or equal to 12, and performing stirring and separating out norazithromycin. The method increases the utilization ratio of the reducing agent, can control reverse reactions of borate, and reduces unnecessary separating process to obtain high quality norazithromycin.