Zidovudine supplier | CasNO.30516-87-1

Name
Zidovudine
EINECS 623-849-4
CAS No. 30516-87-1
Article Data72
CAS DataBase
Density 1.3382 (rough estimate)
Solubility 1-5 g/100 mL at 17 °C in water
Melting Point 106-112 °C
Formula C₁₀H₁₃N₅O₄
Boiling Point 410.43°C (rough estimate)
Molecular Weight 267.244
Flash Point 9℃
Transport Information
Appearance Off -white crystalline powder
Safety 36/37/39-45-36-26
Risk Codes 40-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms 3-Azido-3-deoxythymidine;3'-Azido-3'-deoxythymidine;3'-Azidothymidine;3'-Deoxy-3'-azidothymidine;AZT;AZT (pharmaceutical);Azidothymidine;Azitidin;BW-A 509U;Compound S;NSC602670;Retrovir;Retrovir IV;Retrovis;Timazid;Viro-Z;ZDV;ZVD;Zido-H;
PSA 134.07000
LogP -0.74354

Synthetic route

: 106060-78-0
3'-azido-5'-O-benzoyl-3'-deoxythymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sodium methylate In methanol for 24h; Ambient temperature;	95%
With ammonia In methanol at 20℃;	81%
With sodium methylate In methanol	71%
With ammonia In methanol

: 29706-84-1
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With silica gel; trifluoroacetic acid In methanol; chloroform	95%
With hydrogenchloride In methanol; water at 20℃; for 3h;	95%
With hydrogenchloride In acetic acid at 20℃; for 2h;	49%
With sodium periodate In acetone at 50℃; for 20h;

: 134077-32-0
3'-Azido-5'-O-(4-methoxybenzoyl)-3'-deoxythymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sodium methylate In methanol for 12h; Ambient temperature;	94%
With sodium methylate In methanol

: 162404-30-0
AZT guanidine salt

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With hydrogenchloride In water at 75℃; Large scale reaction;	88.5%

: 126441-74-5
3’-azido-5’-O-(4,4’-dimethoxytrityl)-3’-deoxythymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In methanol; tetrachloromethane at 25 - 40℃; for 12h; ultrasonic;	87%

: 3'-azido-3'-deoxy-5'-O-pivaloylthymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h;	86%

: 52450-18-7
3'-amino-3'-deoxythymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 4h;	83%

: 15981-92-7
2,3'-anhydrothymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide for 3h; Heating;	71%

: 15981-92-7
2,3'-anhydrothymidine

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 3-(3-azido-2,3-dideoxy-β-D-ribofuranosyl)thymine

Conditions

Conditions	Yield
With lithium azide In N,N-dimethyl-formamide at 110℃; for 24h;	A 56% B n/a
With lithium azide In N,N-dimethyl-formamide at 110℃; for 24h; Title compound not separated from byproducts;

: 1-[(4S,5S)-4-Azido-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 66323-40-8
alpha-3'-azido-2',3'-dideoxythymidine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h; Ambient temperature;	A 31% B 45%
With tetrabutyl ammonium fluoride In tetrahydrofuran Yield given. Yields of byproduct given;
With tetrabutyl ammonium fluoride In tetrahydrofuran Yield given;
With tetrabutyl ammonium fluoride In tetrahydrofuran

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: 371164-35-1
4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 73971-82-1
1-(3'-azido-2',3'-dideoxy-β-D-threo-pentofuranosyl)thymine

C: 1-((2S,4R,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

D: 66323-40-8
alpha-3'-azido-2',3'-dideoxythymidine

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 20℃; Further byproducts given;	A 38% B 13% C 12% D 25%

...Expand

: [(2S,3S)-3-Azido-5-(5-methyl-2,4-bis-trimethylsilanyloxy-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-methanol

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 66323-40-8
alpha-3'-azido-2',3'-dideoxythymidine

Conditions

Conditions	Yield
With trifluoroacetic acid for 20h; Ambient temperature;	A 33% B 29%

: 3'-azido-3'-deoxy-5'-O-(2,3-dimercaptopropanoyl)thymidine

A: 99004-90-7
3'-amino-3'-deoxythymidine hydrochloride

B: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With α,α'-azodiizobutyramidine-dihydrochloride In water-d2; d(4)-methanol at 50℃; for 24h; Inert atmosphere;	A Ca. 5 mg B 25%

: 25442-42-6
5'-O-trityl-2,3'-anhydrothymidine

: 29706-84-1
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 65-71-4
thymin

C: 3'-N''-(3'''-azido-3'''-deoxythymid-3''-yl)-3'-deoxythymidine

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 108℃; for 24h;	A 31 %Chromat. B 16 %Chromat. C 8.6%

...Expand

: 25442-42-6
5'-O-trityl-2,3'-anhydrothymidine

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 3-(3-azido-2,3-dideoxy-β-D-ribofuranosyl)thymine

Conditions

Conditions	Yield
With lithium azide; acetic acid 1.) DMF, 150 deg C, 3 h, 2.) 55 deg C, 4 h; Yield given. Multistep reaction. Yields of byproduct given;

: 66323-42-0
1-(5′-O-acetyl-3′-azido-2′,3′-dideoxy-β-D-ribofuranosyl)thymine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: Propionic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: Butyric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: Hexanoic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: Octanoic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: Decanoic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: Dodecanoic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: 130683-74-8
3‘-azido-2’,3’-dideoxy-5’-O-(tetradecanoyl)thymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: Hexadecanoic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: Octadecanoic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In ethanol at 40℃; Rate constant; chemical and enzymatic hydrolysis; var. buffers pH (2.0-9.0); var. temperature;

: 1-((3S,4S)-3-Azido-1-benzyloxy-4,5-dihydroxy-pentyl)-5-methyl-1H-pyrimidine-2,4-dione

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sulfuric acid In methanol Yield given;

: 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 66323-40-8
alpha-3'-azido-2',3'-dideoxythymidine

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Yield given. Yields of byproduct given;

: 123533-06-2
3'-azido-3'-deoxy-5'-O-thexyldimethylsilylthymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With Dowex 50(H+) In methanol
With Dowex 50 x 2 (H+) In methanol Ambient temperature;

: 136011-36-4
1-(3-azido-2,3-dideoxy-β-D-ribo-hexofuranosyl)thymine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With Dowex 1(BH4-); Dowex 1(IO4-) 1) 80percent aq. MeOH, r.t., 1.5 h, 2) r.t., 1.5 h; Yield given. Multistep reaction;

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 147907-41-3
phenyl methoxyleucinyl phosphorochloridate

: 3'-azidothymidine 5'-

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole In tetrahydrofuran for 5h; Ambient temperature;	100%

: [Zn(1-hexadecyl-1,4,7,10-tetraazacyclododecane)(H2O)](ClO4)2 hydrate

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: [Zn(1-hexadecyl-1,4,7,10-tetraazacylodecane)(C10H12N5O4)] (ClO4)

Conditions

Conditions	Yield
With pentaisopropylguanidine In chloroform-d1 addn. of Zn complex to soln. of pentaisopropylguanidine and azidodeoxythymidine; (1)H-NMR-monitoring;	100%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

poly(oxyethylene H-phosphonate): poly(oxyethylene H-phosphonate)

poly(5'-O-3'-azido-2',3'-dideoxythymidine-oxyethylene phosphate): poly(5'-O-3'-azido-2',3'-dideoxythymidine-oxyethylene phosphate)

Conditions

Conditions	Yield
With triethylamine In tetrachloromethane; 1,2-dichloro-ethane; acetonitrile at 20℃; for 24h;	100%

: 7693-45-0
4-Chlorophenyl chloroformate

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 1355331-53-1
C17H16ClN5O6

Conditions

Conditions	Yield
With pyridine	100%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 133101-33-4
1,2,3,4-tetra-O-acetyl-6-D-glucose phosphate pyridinium form

: 1,2,3,4-tetra-O-acetyl-6-D-glucopyranosyl-3'-azido-3'-deoxy-5'-thymidinyl phosphate

Conditions

Conditions	Yield
In pyridine	99%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 147907-40-2
phenyl (methoxyglycinyl)phosphorochloridate

: 3'-azidothymidine 5'-

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole In tetrahydrofuran for 12h; Ambient temperature;	99%

: 186581-53-3, 908094-01-9
diazomethane

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 108441-46-9
3'-azido-3'-deoxy-3-methylthymidine

Conditions

Conditions	Yield
In diethyl ether; ethanol at 0℃; for 0.5h;	99%

: benzyl (R)-3-(2-(((8R,9S,13S,14S,17S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)oxy)ethyl)-2-methylenepent-4-ynoate

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: benzyl (S)-3-(1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-1H-1,2,3-triazol-4-yl)-5-(((8R,9S,13S,14S,17S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)oxy)-2-methylenepentanoate

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 12h; Inert atmosphere; Schlenk technique;	99%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 1609-47-8
diethyl dicarbonate

: 3'-azido-3'-deoxy-5'-O-ethoxycarbonylthymidine

Conditions

Conditions	Yield
With dmap In pyridine for 1h; Ambient temperature;	98%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 147907-39-9
(4-fluorophenoxy)(((1S)-(1-methoxycarbonylethyl))amino)phosphinylchloride

: 3'-azidothymidine 5'-

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole In tetrahydrofuran for 12h; Ambient temperature;	97%
With 1-methyl-1H-imidazole In tetrahydrofuran

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 52450-18-7
3'-amino-3'-deoxythymidine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol	97%
With hydrogen; palladium on activated charcoal In methanol	92%
With hydrogen; palladium on activated charcoal at 20℃; for 6h; Reduction;	87%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 98-59-9
p-toluenesulfonyl chloride

: 64638-13-7
3'-Azido-3',5'-dideoxythymidine-5'-O-tosylthymidine

Conditions

Conditions	Yield
With pyridine for 96h; Ambient temperature;	97%
With pyridine	96%
With pyridine Ambient temperature;	74%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 1048636-94-7
2',5'-dideoxy-5'-ethynyl-3'-epi-thymidine

: C22H27N7O8

Conditions

Conditions	Yield
With copper bromide dimethyl sulfide complex In tetrahydrofuran; water; tert-butyl alcohol at 80℃; for 1h; Huisgen reaction; Microwave irradiation;	97%
With dimethylsulfide; triethylamine In tetrahydrofuran; water; tert-butyl alcohol at 80℃; for 1h; Microwave irradiation;	25.1 mg

: 1033098-90-6
2-propyn-1-yl 2,3,4-tri-O-acetyl-β-D-xylopyranose

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 1108170-91-7
C24H31N5O12

Conditions

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 24h; Huisgen cycloaddition;	96.9%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 147907-38-8
(4‐methoxy)phenyl (methoxy‐L‐alaninyl)phosphorochloridate

: 149560-32-7
3'-azidothymidine 5'-[p-methoxyphenyl methoxyalaninyl phosphate]

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole In tetrahydrofuran for 16h; Ambient temperature;	96%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 108-24-7
acetic anhydride

: 66323-42-0
1-(5′-O-acetyl-3′-azido-2′,3′-dideoxy-β-D-ribofuranosyl)thymine

Conditions

Conditions	Yield
With pyridine at 20℃;	96%
With pyridine at 20℃; for 8h;	94%
With pyridine Ambient temperature;

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 67373-56-2
chlorodimethyl(1,1,2-trimethylpropyl)silane

: 123533-06-2
3'-azido-3'-deoxy-5'-O-thexyldimethylsilylthymidine

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 2h; Ambient temperature;	96%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 120624-97-7
1-{(2R,4S,5S)-4-azido-5-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}tetrahydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide	96%
With 1H-imidazole In acetonitrile at 20℃;	92%
With 1H-imidazole at 20℃; for 12h; Inert atmosphere;	91%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 34272-02-1
1-O-propargyl 2,3,4,6-tetra-O-acetyl-β-D-glucose

: 1108170-87-1
C27H35N5O14

Conditions

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 24h; Huisgen cycloaddition;	96%

: 766-98-3
1-ethynyl-4-fluorobenzene

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 127479-75-8
3′-deoxy-3′-[4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl]-thymidine

Conditions

Conditions	Yield
With copper; copper(II) sulfate In water; tert-butyl alcohol at 125℃; for 0.333333h; Huisgen 1,3-dipolar cycloaddition; Microwave irradiation; regioselective reaction;	96%
With copper(ll) sulfate pentahydrate; L-ascorbic acid sodium salt In tetrahydrofuran; water at 20℃; for 12h;

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 107-19-7
propargyl alcohol

: 127479-69-0
1-((2R,4S,5S)-5-(hydroxymethyl)-4-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 12h; Huisgen Cycloaddition; Inert atmosphere;	96%
With copper; copper(II) sulfate In water; tert-butyl alcohol at 125℃; for 0.166667h; Huisgen 1,3-dipolar cycloaddition; Microwave irradiation; regioselective reaction;	80%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 12h; Huisgen Cycloaddition;

: 17061-86-8
1-methoxy-4-(2-propynyloxy)benzene

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 1310031-49-2
C20H23N5O6

Conditions

Conditions	Yield
Stage #1: 1-methoxy-4-(2-propynyloxy)benzene; 3'-azido-2',3'-deoxythymidine In water; tert-butyl alcohol at 20℃; for 0.166667h; Stage #2: With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃;	96%

: 20009-28-3
naphth-2-yloxymethylacetylene

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 1310031-51-6
1-((2R,4S,5S)-5-(hydroxymethyl)-4-(4-((naphthalen-2-yloxy)-methyl)-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
Stage #1: naphth-2-yloxymethylacetylene; 3'-azido-2',3'-deoxythymidine In water; tert-butyl alcohol at 20℃; for 0.166667h; Stage #2: With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃;	96%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 12h; Huisgen Cycloaddition; Inert atmosphere;	84%

: C14H13NO3

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 1-((2R,4S,5S)-5-(hydroxymethyl)-4-(4-(((3-(4-methoxyphenyl)isoxazol-5-yl)methoxy) methyl)-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With copper(II) acetate monohydrate; sodium L-ascorbate In isopropyl alcohol at 45℃; for 0.166667h; Wavelength; UV-irradiation;	96%

: N-[3β-O-(3’,3’-dimethylsuccinyl)-2α-propargyl-lup-20(29)-en-28-oyl]-N’-(tert-butoxycarbonyl)-8-octylamine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: [1-(3’-deoxythymidine)-1H-1,2,3-triazol-4-yl]-{[N-2α-methyl-3β-O-(3’,3’-dimethylsuccinyl)-lup-20,29-en-28-oyl]-N’-(tert-butoxycarbonyl)}-8-octylamine

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In dimethyl sulfoxide at 20℃; for 2h;	96%

: C24H35NO

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: C34H48N6O5

Conditions

Conditions	Yield
With copper(I) thiophene-2-carboxylate In toluene at 50℃;	96%

: 108-30-5
succinic acid anhydride

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 106060-83-7
4-((3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)-4-oxobutanoic acid

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 20℃; for 18h;	95%
With pyridine; dmap at 20℃; for 4h;	94%
With dmap In N,N-dimethyl-formamide at 20℃; for 14h;	85%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 88-10-8
N,N-diethylcarbamyl chloride

: 3'-azido-3'-deoxy-5'-O-diethylcarbamoylthymidine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 36h; Ambient temperature;	95%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: (S)-3-Phenyl-2-(2-thioxo-2λ5-[1,3,2]dithiaphospholan-2-ylamino)-propionic acid methyl ester

: C20H25N6O6PS2

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Condensation;	95%

Zidovudine History

Usage of Zidovudine was major breakthrough in AIDS therapy in the 1990s that significantly altered the course of the illness and helped destroy the notion of the 1980s and early 90s that HIV/AIDS was an instant death sentence.
Jerome Horwitz of Barbara Ann Karmanos Cancer Institute and Wayne State University School of Medicine first synthesized Zidovudine in 1964, under a US National Institutes of Health (NIH) grant. Zidovudine was originally intended as an anticancer drug, but was shelved after it proved insufficiently toxic to cancer tumours in mice.

Zidovudine Specification

The IUPAC name of Zidovudine is 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione. With the CAS registry number 30516-87-1, it is also named as 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)-5-methylpyrimidine-2,4-(1H,3H)-dione. It is off -white crystalline powder which is a dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. When burns, it will produce toxic nitrogen oxide fumes. Additionally, this chemical should be sealed in the container and stored at -20 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.53; (4)ACD/LogD (pH 7.4): -0.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.29; (8)ACD/KOC (pH 7.4): 12.12; (9)#H bond acceptors: 9; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 71.44 Å²; (13)Rotatable Bond Count: 3; (14)Tautomer: Count 3; (15)Exact Mass: 267.096754; (16)MonoIsotopic Mass: 267.096754; (17)Topological Polar Surface Area: 93.2; (18)Heavy Atom Count: 19; (19)Complexity: 484; (20)Defined Atom StereoCenter Count: 3.

Preparation of Zidovudine: It can be obtained by thymidine, triphenylphosphine, p-methoxybenzo and Diethyl azodicarboxylate.

Uses of Zidovudine: It is a type of antiretroviral drug used for the treatment of HIV/AIDS. Its use was a major breakthrough in AIDS therapy in the 1990s that significantly altered the course of the illness and helped destroy the notion that HIV/AIDS was a death sentence. This drug is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Chronic, high-dose therapy with Zidovudine is associated with significant side effects, including anemia, neutropenia, hepatotoxicity, cardiomyopathy, and myopathy.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. It also has limited evidence of a carcinogenic effect. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. Smiles:n1([C@H]2C[C@H](N=[N+]=[N-])[C@H](O2)CO)c([nH]c(=O)c(c1)C)=O
2. InChI:InChI=1/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	LDLo	oral	86mg/kg/1W-I (86mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: HEADACHE	Lancet. Vol. 2, Pg. 1392, 1986.
man	TDLo	oral	434mg/kg/38D- (434mg/kg)	BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE BLOOD: APLASTIC ANEMIA	Annals of Internal Medicine. Vol. 107, Pg. 502, 1987.
man	TDLo	unreported	69mg/kg (69mg/kg)	SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE"	Annals of Internal Medicine. Vol. 114, Pg. 297, 1991.
mouse	LD50	intravenous	> 70mg/kg (70mg/kg)		United States Patent Document. Vol. #4804651,
mouse	LD50	oral	3062mg/kg (3062mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996.
mouse	LD50	unreported	> 750mg/kg (750mg/kg)		United States Patent Document. Vol. #4857511,
rat	LD50	intravenous	> 70mg/kg (70mg/kg)		United States Patent Document. Vol. #4804651,
rat	LD50	oral	3084mg/kg (3084mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996.
rat	LD50	unreported	> 750mg/kg (750mg/kg)		United States Patent Document. Vol. #4857511,
women	TDLo	oral	1gm/kg/6W-I (1000mg/kg)	SKIN AND APPENDAGES (SKIN): NAILS: OTHER	Annals of Internal Medicine. Vol. 107, Pg. 350, 1987.

Product Name

Zidovudine

Synthetic route

Zidovudine History

Zidovudine Specification

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