Product Name

  • Name

    Stavudine

  • EINECS 641-374-0
  • CAS No. 3056-17-5
  • Article Data76
  • CAS DataBase
  • Density 1.374 g/cm3
  • Solubility Water solubility: 5-10 g/100 mL at 21 °C
  • Melting Point 159-160 °C
  • Formula C10H12N2O4
  • Boiling Point
  • Molecular Weight 224.216
  • Flash Point
  • Transport Information
  • Appearance white powder
  • Safety 26-S36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3056-17-5 (Stavudine)
  • Hazard Symbols IrritantXi
  • Synonyms Thymidine,2',3'-didehydro-3'-deoxy-;Thymine,1-(2,3-dideoxy-b-D-glycero-pent-2-enofuranosyl)- (7CI,8CI);2'-Thymidinene, 3'-deoxy- (8CI);2',3'-Didehydro-3'-deoxythymidine;3'-Deoxy-2',3'-didehydrothymidine;Avostav;BMY 27857;D 4T (nucleoside);NSC163661;Stag;Stavir;Virostav;Zerit;d4T;
  • PSA 84.32000
  • LogP -0.70910

Synthetic route

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>thymine
125440-17-7

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1.5h; Ambient temperature;100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃;90%
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;78%
With tetrabutyl ammonium fluoride In tetrahydrofuran Yield given;
1-<2',3'-dideoxy-3'(R)-phenylseleno-β-D-glycero-pentofuranosyl>thymine
131933-47-6

1-<2',3'-dideoxy-3'(R)-phenylseleno-β-D-glycero-pentofuranosyl>thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In tetrahydrofuran 1) 0 deg C, 0.25 h, 2) warm to RT, 1 h;99%
1-(5-0-Pivaloyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
126209-27-6

1-(5-0-Pivaloyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With sodium methylate In methanol at 23℃; for 4h;95%
With buffer In ethanol at 40℃; Rate constant; hydrolysis, also enzymatic hydrolysis; various pH-values;
2,3'-anhydrothymidine
15981-92-7

2,3'-anhydrothymidine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With 1-(2-methoxyethyl)-3-methylimidazolium trifluoroacetate; sodium hydride In mineral oil at 100℃; for 0.0833333h;93%
With sodium hydride In N,N-dimethyl acetamide at 100℃; for 0.5h;81%
5'-O-benzoyl-2',3'-didehydro-3'-deoxythymidine
122567-97-9

5'-O-benzoyl-2',3'-didehydro-3'-deoxythymidine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With sodium methylate In methanol Ambient temperature;92%
With N-butylamine at 70℃; for 6h;90%
With N-butylamine90%
1-{5-[bis(4-methoxyphenyl)phenyl-methoxymethyl]-2,5-dihydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione
149666-71-7

1-{5-[bis(4-methoxyphenyl)phenyl-methoxymethyl]-2,5-dihydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
In methanol; tetrachloromethane at 25 - 40℃; for 3h; ultrasonic;92%
With methanol; Dowex 50W H(1+) form for 0.166667h;90%
stavudine N,N-dimethylacetamide solvate

stavudine N,N-dimethylacetamide solvate

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
In water; isopropyl alcohol at 0 - 70℃; for 1.33333h; Purification / work up;91.4%
In water; acetone at 0℃; for 2.16667h; Purification / work up;76%
In water at 0 - 65℃; for 2.33333h; Purification / work up;73.7%
2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate
938050-90-9

2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
Stage #1: 2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate In water; isopropyl alcohol at 82℃;
Stage #2: In isopropyl alcohol at 0 - 5℃; for 1.5h; Purification / work up;		87.2%
In isopropyl alcohol at 0 - 82℃; for 1.5h; Product distribution / selectivity;87.2%
Stage #1: 2',3'-didehydro-3'-deoxythymidine N,N-dimethyl propylene urea solvate In water; acetone at 55℃;
Stage #2: In acetone at 0 - 40℃; for 1h; Purification / work up;		84%
1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine
77421-68-2

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Ambient temperature;87%
With sodium hydroxide In acetonitrile for 0.5h; Yield given;
With buffer In ethanol at 40℃; Rate constant; hydrolysis, also enzymatic hydrolysis; various pH-values;
1-(2,3-dideoxy-3-C-selenophenyl-β-D-erythro-pentofuranosyl)thymine
131933-44-3

1-(2,3-dideoxy-3-C-selenophenyl-β-D-erythro-pentofuranosyl)thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In tetrahydrofuran 1) 0 deg C, 0.25 h, 2) warm to RT, 1 h;86%
hydrated p-toluene sulfonate

hydrated p-toluene sulfonate

tributyl-amine
102-82-9

tributyl-amine

ammonium hydroxide

ammonium hydroxide

5-Methyluridine
1463-10-1

5-Methyluridine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With sodium methylate; acetic anhydride; sodium carbonate; hydrous zirconium oxide In methanol86%
...Expand
3',4'-anhydrothymidine
7481-90-5

3',4'-anhydrothymidine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With potassium hydroxide In tert-butyl alcohol at 55 - 60℃; for 2h;85%
With sodium hydride In N,N-dimethyl acetamide at 100℃; for 0.75h;76%
With potassium tert-butylate In dimethyl sulfoxide at 21℃; for 17h;57%
1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
119794-55-7

1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran80%
5'-O-t-butyl-dimethylsilyl-3'-O-methanesulfonyl-thymidine
117383-83-2

5'-O-t-butyl-dimethylsilyl-3'-O-methanesulfonyl-thymidine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide for 0.5h; Ambient temperature;80%
1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine
5964-41-0

1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With acetic acid at 50℃; for 1h;71%
With acetic acid In water at 80 - 90℃; for 1h;67%
With acetic acid
5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N3-(4-methoxybenzyl)-5-methyluridine
161824-93-7

5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N3-(4-methoxybenzyl)-5-methyluridine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetonitrile for 3h; Ambient temperature;68%
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
4336-39-4

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
Stage #1: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate With palladium diacetate; lithium bromide In N,N-dimethyl-formamide at 180℃; for 36h; Inert atmosphere;
Stage #2: With sodium methylate In methanol at 20℃; for 3h; Concentration; Temperature; Reagent/catalyst; Solvent;		68%
1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine
152039-45-7

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 48h; Heating;60%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 24h; Heating; Yield given;
1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine
110483-43-7

1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With copper; zinc In methanol for 0.5h;53%
Multi-step reaction with 2 steps
1: tetraethylammonium p-toluenesulfonate / methanol / 1 h / Electrolysis; Pt plate anode, Hg pool cathode
2: NH4OH
View Scheme
Multi-step reaction with 2 steps
1: 1.) zinc powder, 2.) aq. EDTA sodium salt / 1.) CH3CN, RT, 2 h
2: aq. NaOH / acetonitrile / 0.5 h
View Scheme
Multi-step reaction with 2 steps
1: 53 percent / Zn/Cu / methanol / 0.5 h
2: 87 percent / sodium methoxide / methanol / 2 h / Ambient temperature
View Scheme
1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-methylsulfonyl-α,β-D-erythro-pentofuranosyl)thymine
139212-94-5, 139212-95-6

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-methylsulfonyl-α,β-D-erythro-pentofuranosyl)thymine

A

2,3'-anhydrothymidine
15981-92-7

2,3'-anhydrothymidine

B

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 24h; Ambient temperature;A 52%
B 17%
1-(2',3'-dideoxy-2'-iodo-5'-O-(trimethylacetyl)-β-D-ribofuranosyl)thymine
144867-91-4

1-(2',3'-dideoxy-2'-iodo-5'-O-(trimethylacetyl)-β-D-ribofuranosyl)thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With sodium methylate In methanol48%
With sodium methylate In methanol at 20℃; for 18h; Yield given;
Multi-step reaction with 3 steps
1: DBU / CH2Cl2 / 1 h / 0 °C
2: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C
3: 95 percent / sodium methoxide / methanol / 4 h / 23 °C
View Scheme
1-(3,5-anhydro-2-deoxy-β-D-threo-pentofuranosyl)-2-O-ethylthymine
155807-21-9

1-(3,5-anhydro-2-deoxy-β-D-threo-pentofuranosyl)-2-O-ethylthymine

A

2-methyl-5-(thymin-1-yl)furan
5983-11-9

2-methyl-5-(thymin-1-yl)furan

B

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide for 1h; Ambient temperature;A 32.5%
B 3.5%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

3',4'-anhydrothymidine
7481-90-5

3',4'-anhydrothymidine

A

1-((2R,4R,5R)-4-Hydroxy-5-pentyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
124685-30-9

1-((2R,4R,5R)-4-Hydroxy-5-pentyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

B

thymin
65-71-4

thymin

C

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -70℃; for 1h;A 31%
B 18%
C 13%
...Expand
tert.-butyl lithium
594-19-4

tert.-butyl lithium

3',4'-anhydrothymidine
7481-90-5

3',4'-anhydrothymidine

A

1-[(2R,4R,5R)-5-(2,2-Dimethyl-propyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
124685-31-0

1-[(2R,4R,5R)-5-(2,2-Dimethyl-propyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

B

1-(2,5-dideoxy-β-D-threo-pentofuranosyl)thymine
118778-33-9

1-(2,5-dideoxy-β-D-threo-pentofuranosyl)thymine

C

thymin
65-71-4

thymin

D

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran; pentane at -70℃; for 1h; Yields of byproduct given;A 26%
B n/a
C 27%
D n/a
With boron trifluoride diethyl etherate In tetrahydrofuran; pentane at -70℃; for 1h; Yield given. Yields of byproduct given;A 26%
B n/a
C 27%
D n/a
With boron trifluoride diethyl etherate In tetrahydrofuran; pentane at -70℃; for 1h; Yield given;A 26%
B n/a
C 27%
D n/a
...Expand
Acetic acid (2R,3R,4R,5R)-4-bromo-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Acetic acid (2R,3R,4R,5R)-4-bromo-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

A

(E)-1-(3(S),4(R),5-trihydroxypent-1-en-1-yl)thymine
127516-98-7

(E)-1-(3(S),4(R),5-trihydroxypent-1-en-1-yl)thymine

B

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With ammonia; copper; acetic acid; zinc 1.) DMF, RT, 30 min; Yield given. Multistep reaction. Yields of byproduct given;
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine
42214-24-4

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

A

stavudin
3056-17-5

stavudin

B

alovudine
25526-93-6

alovudine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; acetic acid 1.) THF, RT, 32 h, 2.) 110 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;
With diethylamino-sulfur trifluoride; acetic acid 1.) THF, benzene, 2 h, 2.) 100 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;
1-(2-deoxy-3,5-epoxy-β-D-threo-pentofuranosyl)thymine
38313-48-3

1-(2-deoxy-3,5-epoxy-β-D-threo-pentofuranosyl)thymine

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide
With potassium hydroxide In isopropyl alcohol Rearrangement;
Octanoic acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester

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

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With buffer In ethanol at 40℃; Rate constant; hydrolysis, also enzymatic hydrolysis; various pH-values;
2',3'-didehydro-3'-deoxythymidine 5'-O-hemisuccinate
152336-78-2

2',3'-didehydro-3'-deoxythymidine 5'-O-hemisuccinate

stavudin
3056-17-5

stavudin

Conditions
ConditionsYield
With buffer In ethanol at 40℃; Rate constant; hydrolysis, also enzymatic hydrolysis; various pH-values;

STAVUDINE Chemical Properties

IUPAC Name:1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
Molecular Formula:C10H12N2O4
Molecular Weight:224.213280：
Melting Point:159-160°C
refractive index:-46 ° (C=0.69, H2O)
storage temp.:20°C
Water Solubility:5-10 g/100 mL at 21°C
CAS DataBase Reference:3056-17-5(CAS DataBase Reference)
EPA Substance Registry System:3056-17-5(EPA Substance)
Synonyms of STAVUDINE(3056-17-5):
STAVUDINE;ZERIT;3'-deoxythymidin-2'-ene;3'-DEOXY-2',3'-DIDEHYDROTHYMIDINE;1-((2R,5S)-5-HYDROXYMETHYL-2,5-DIHYDRO-FURAN-2-YL)-5-METHYL-1H-PYRIMIDINE-2,4-DIONE;1-[2,3-DIDEOXY-BETA-D-GLYCERO-PENT-2-ENOFURANOSYL]THYMINE;2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE;2',3'-DIHYDRO-2',3'-DEOXYTHYMIDINE
Categories of STAVUDINE(3056-17-5):
Active Pharmaceutical Ingredients;chiral;Antivirals for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides;Pharmaceuticals;API's

STAVUDINE History

STAVUDINE(3056-17-5) was the fourth antiretroviral drug on the market, its patent expired in the United States on 2008-06-25.
STAVUDINE(3056-17-5) was first synthetized in the sixties by Jerome Horwitz,subsequently reconsidered as an anti-HIV agent by the Rega Institute for Medical Research in Belgium.
STAVUDINE(3056-17-5) was approved by the U.S.FDA in Jun 24, 1994 for adults and in Sep 6, 1996 for pediatric use.
STAVUDINE(3056-17-5) was approved by the U.S.FDA  for once-a-day dosing in 2001.

STAVUDINE Uses

STAVUDINE(3056-17-5) is used as a antiviral drug.

STAVUDINE Toxicity Data With Reference

1.   

dni-hmn-lym 20 µmol/L

   MOPMA3    Molecular Pharmacology. 39 (1991),625.
2.   

cyt-orl-mus 600 mg/kg/3D-C

   EMMUEG    Environmental and Molecular Mutagenesis. 18 (1991),168.
3.   

orl-rat LD50:4 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
4.   

ivn-rat LD50:>1200 mg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
5.   

orl-mus LD50:1 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
6.   

ivn-mus LD50:1 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
7.   

orl-dog LD :>2 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.
8.   

ivn-dog LD :>1680 mg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),1944.

STAVUDINE Safety Profile

Safety Information of STAVUDINE(3056-17-5):
Hazard Codes:Xi 
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin 
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing   
WGK Germany:2
RTECS:XP2075000
Hazardous Substances Data:3056-17-5(Hazardous Substances Data)
Moderately toxic by ingestion and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

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