Thymine 1-beta-D-arabinofuranoside supplier

Name
THYMINE-BETA-D-ARABINOFURANOSIDE
EINECS 210-083-7
CAS No. 605-23-2
Article Data20
CAS DataBase
Density 1.576g/cm³
Solubility
Melting Point
Formula C₁₀H₁₄N₂O₆
Boiling Point
Molecular Weight 258.231
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Thymine,1-b-D-arabinofuranosyl-(6CI,7CI,8CI);1-b-DArabinofuranosylthymine;1-b-D-Arabinofuranosylthymine;5-Methylarabinosyluracil;Ara-T;Arabinosylthymine;NSC 68929;Spongothymidin;Spongothymidine;Thyminearabinoside;
PSA 124.78000
LogP -2.54350

Synthetic route

: 22423-26-3
O-2,2'-cyclo-5-methyluridine

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
With ammonium hydroxide at 70℃; for 14h;	100%
With sodium hydroxide at 22℃; for 2h; Rate constant;
With sodium hydroxide at 37℃;

: 88054-44-8
5-(p-tolylthiomethyl)-1-β-D-arabinofuranosyluracil

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
With nickel In ethanol Heating;	66%

: 2,2'-anhydro-5'-O-tert-butyldiphenylsilyl-3'-O-ethylphosphonoacetyl-5-methyluridine

A: 171763-19-2
5'-O-tert-butyldiphenylsilyl-O2-2'-anhydro-5-methyluridine

B: 1-(5-O-tert-butyldiphenylsilyl-β-D-arabinofuranosyl)thymine

C: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water at 20℃; for 0.333333h; Hydrolysis; Alkaline hydrolysis;	A 65% B 25% C n/a

...Expand

: 1463-10-1
5-Methyluridine

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
With bis(phenyl) carbonate; copper; sodium hydrogencarbonate In N,N-dimethyl-formamide at 140 - 150℃; for 45h;	50%
With hydrogenchloride; O-acetylsalicyloyl chloride 1.) nitromethane, 20 deg C, 15 h, 2.) water, dioxane, 100 deg C, 2.5 h; Yield given. Multistep reaction;
With hydrogenchloride; O-acetylsalicyloyl chloride 2.) water, dioxane; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: pyridine 2: aufeinanderfolgende Behandlung des Reaktionsprodukts mit methanol.NH3 und mit wss.H2SO4 View Scheme

: 2-((3aR,5R,6R,6aS)-6-Hydroxy-5-hydroxymethyl-2-imino-tetrahydro-furo[2,3-d]oxazol-3-ylmethyl)-acrylic acid ethyl ester; hydrobromide

A: 22423-26-3
O-2,2'-cyclo-5-methyluridine

B: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 25℃; for 20h;	A 32% B 14%

: 124-63-0
methanesulfonyl chloride

: 101796-28-5
1-(5'-O-trityl-β-D-ribofuranosyl)thymine

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
aufeinanderfolgende Behandlung des Reaktionsprodukts mit methanol.NH3 und mit wss.H2SO4;

: 75-24-1
trimethylaluminum

: 111582-87-7
1-((2R,3S,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-4-trimethylsilanyloxy-1H-pyrimidin-2-one

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
With water; ammonium chloride; triphenylphosphine 1) THF, reflux, 12 h, 2) MeOH, reflux, 3 h; Yield given. Multistep reaction;

: 75-24-1
trimethylaluminum

: 111582-88-8
1-((2R,3S,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-iodo-4-trimethylsilanyloxy-1H-pyrimidin-2-one

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
With water; ammonium chloride; triphenylphosphine 1) THF, reflux, 24 h, 2) MeOH, reflux, 3 h; Yield given. Multistep reaction;

: 25545-03-3
β-D-arabinofuranose

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent 2: 95 percent / N,N-dimethyl-acetamide / Ambient temperature 3: 32 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 20 h / 25 °C 4: 100 percent / aq. ammonia / 14 h / 70 °C View Scheme
Multi-step reaction with 3 steps 1: 96 percent 2: 95 percent / N,N-dimethyl-acetamide / Ambient temperature 3: 14 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 20 h / 25 °C View Scheme

: 27963-98-0
2-amino-β-D-arabinofurano[1',2':4,5]-oxazoline

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / N,N-dimethyl-acetamide / Ambient temperature 2: 32 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 20 h / 25 °C 3: 100 percent / aq. ammonia / 14 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: 95 percent / N,N-dimethyl-acetamide / Ambient temperature 2: 14 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 20 h / 25 °C View Scheme

: 2-((3aR,5R,6R,6aS)-6-Hydroxy-5-hydroxymethyl-2-imino-tetrahydro-furo[2,3-d]oxazol-3-ylmethyl)-acrylic acid ethyl ester; hydrobromide

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 32 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 20 h / 25 °C 2: 100 percent / aq. ammonia / 14 h / 70 °C View Scheme

: 3083-77-0
araU

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: H2O / 0.25 h / Heating 2: ethanol / 0.25 h / Heating 3: 66 percent / Raney-Ni / ethanol / Heating View Scheme

: 88054-41-5
1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-pyrrolidin-1-ylmethyl-1H-pyrimidine-2,4-dione

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 0.25 h / Heating 2: 66 percent / Raney-Ni / ethanol / Heating View Scheme

: 58-63-9
Inosine

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Escherichia coli purine nucleoside phosphorylase 2: 45 percent / uridine phosphorylase 3: 1.) acetylsalicyloyl chloride, 2.) 0.5 N HCl / 2.) water, dioxane View Scheme
Multi-step reaction with 2 steps 1: 45 percent / BM-11 E. coli cells, 0.015 M potassium phosphate buffer (pH 7.25); 1.) 60 deg C, 2 h, 2.) 4 deg C, 18 h 2: 1.) acetylsalicylic chloroanhydride, 2.) 0.5 N HCl / 1.) nitromethane, 20 deg C, 15 h, 2.) water, dioxane, 100 deg C, 2.5 h View Scheme

: 18646-11-2
α-D-ribofuranosyl-1-phosphate

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 45 percent / uridine phosphorylase 2: 1.) acetylsalicyloyl chloride, 2.) 0.5 N HCl / 2.) water, dioxane View Scheme

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / SnCl4 / 1,2-dichloro-ethane / 48 h / 20 °C 2: 80 percent / 1 N sodium methylate / methanol / 3 h / 20 °C 3: 1.) acetylsalicylic chloroanhydride, 2.) 0.5 N HCl / 1.) nitromethane, 20 deg C, 15 h, 2.) water, dioxane, 100 deg C, 2.5 h View Scheme

: 3180-76-5
2',3',5'-tri-O-benzoyluridine

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / 1 N sodium methylate / methanol / 3 h / 20 °C 2: 1.) acetylsalicylic chloroanhydride, 2.) 0.5 N HCl / 1.) nitromethane, 20 deg C, 15 h, 2.) water, dioxane, 100 deg C, 2.5 h View Scheme

: 65-71-4
thymin

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 45 percent / BM-11 E. coli cells, 0.015 M potassium phosphate buffer (pH 7.25); 1.) 60 deg C, 2 h, 2.) 4 deg C, 18 h 2: 1.) acetylsalicylic chloroanhydride, 2.) 0.5 N HCl / 1.) nitromethane, 20 deg C, 15 h, 2.) water, dioxane, 100 deg C, 2.5 h View Scheme
Multi-step reaction with 4 steps 1: ammonium sulfate / 2 h / Heating 2: 93 percent / SnCl4 / 1,2-dichloro-ethane / 48 h / 20 °C 3: 80 percent / 1 N sodium methylate / methanol / 3 h / 20 °C 4: 1.) acetylsalicylic chloroanhydride, 2.) 0.5 N HCl / 1.) nitromethane, 20 deg C, 15 h, 2.) water, dioxane, 100 deg C, 2.5 h View Scheme

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

: 605-23-2
thymine arabinoside

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / SnCl4 / 1,2-dichloro-ethane / 48 h / 20 °C 2: 80 percent / 1 N sodium methylate / methanol / 3 h / 20 °C 3: 1.) acetylsalicylic chloroanhydride, 2.) 0.5 N HCl / 1.) nitromethane, 20 deg C, 15 h, 2.) water, dioxane, 100 deg C, 2.5 h View Scheme

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 605-23-2
thymine arabinoside

: 161602-00-2
1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]thymine

Conditions

Conditions	Yield
With pyridine at 22 - 25℃; for 20h;	93%
With pyridine at 20℃;

: 605-23-2
thymine arabinoside

: 21052-26-6
Phosphoric acid mono-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

Conditions

Conditions	Yield
With tris(p-nitrophenyl)phosphate at 50℃; Erwina herbicola 47/3 cells;	46%

: 624-67-9
Propargylic aldehyde

: 605-23-2
thymine arabinoside

: 90029-89-3
3-(3-oxoprop-1-enyl)-2'β-hydroxythymidine

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at -78℃; for 2h;	28%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 605-23-2
thymine arabinoside

: 1-{(2R,3S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With pyridine

: 371-76-6
bis(trifluoromethyl)mercury

: 605-23-2
thymine arabinoside

: 102302-70-5
1-β-D-arabinofuranosyl-4-O-(difluoromethyl)thymine

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide 1.) 120 deg C; 2.) THF, reflux; Yield given. Multistep reaction;

: 108-24-7
acetic anhydride

: 605-23-2
thymine arabinoside

: 22423-27-4
5-methyl-1-(tri-O-acetyl-β-D-arabinofuranosyl)-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With dmap at 20℃;

: 605-23-2
thymine arabinoside

: 1-β-D-arabinofuranosyl-4-thio-5-methyluracil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 4-dimethylaminopyridine / 20 °C 2: Lawesson's reagent / dioxane / Heating 3: NH3 / methanol / 3 h / 20 °C View Scheme

: 605-23-2
thymine arabinoside

: 22423-28-5
5-methyl-4-thioxo-1-(tri-O-acetyl-β-D-arabinofuranosyl)-3,4-dihydro-1H-pyrimidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4-dimethylaminopyridine / 20 °C 2: Lawesson's reagent / dioxane / Heating View Scheme

: 605-23-2
thymine arabinoside

: 937028-16-5
1-[2-O-octanoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]thymine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / pyridine / 20 h / 22 - 25 °C 2: 50 percent / pyridine / Heating View Scheme

: 605-23-2
thymine arabinoside

: 1-(2-O-octanoyl-β-D-arabinofuranosyl)thymine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / pyridine / 20 h / 22 - 25 °C 2: 50 percent / pyridine / Heating 3: 50 percent / ammonium fluoride; Dowex(R) H(+) form resin / methanol / 22 - 25 °C View Scheme

: 605-23-2
thymine arabinoside

: 1-(2-O-pentanoyl-β-D-arabinofuranosyl)thymine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / pyridine / 20 h / 22 - 25 °C 2: 68 percent / pyridine / Heating 3: 60 percent / ammonium fluoride; Dowex(R) H(+) form resin / methanol / 22 - 25 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine / 20 °C 2: pyridine / Heating 3: NH4F; Dowex H+ form 50x2-100 / methanol / 20 °C View Scheme

: 605-23-2
thymine arabinoside

: 1-(2-O-decanoyl-β-D-arabinofuranosyl)thymine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / pyridine / 20 h / 22 - 25 °C 2: 58 percent / pyridine / Heating 3: 42 percent / ammonium fluoride; Dowex(R) H(+) form resin / methanol / 22 - 25 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine / 20 °C 2: pyridine / Heating 3: NH4F; Dowex H+ form 50x2-100 / methanol / 20 °C View Scheme

: 605-23-2
thymine arabinoside

: 1-(2-O-dodecanoyl-β-D-arabinofuranosyl)thymine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / pyridine / 20 h / 22 - 25 °C 2: 95 percent / pyridine / Heating 3: 50 percent / ammonium fluoride; Dowex(R) H(+) form resin / methanol / 22 - 25 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine / 20 °C 2: pyridine / Heating 3: NH4F; Dowex H+ form 50x2-100 / methanol / 20 °C View Scheme

: 605-23-2
thymine arabinoside

: 351523-13-2
1-[2-O-pentanoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]thymine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / pyridine / 20 h / 22 - 25 °C 2: 68 percent / pyridine / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: pyridine / Heating View Scheme

: 605-23-2
thymine arabinoside

: 351523-05-2
1-[2-O-decanoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]thymine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / pyridine / 20 h / 22 - 25 °C 2: 58 percent / pyridine / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: pyridine / Heating View Scheme

: 605-23-2
thymine arabinoside

: 351523-14-3
1-[2-O-dodecanoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]thymine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / pyridine / 20 h / 22 - 25 °C 2: 95 percent / pyridine / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: pyridine / Heating View Scheme

Thymine 1-beta-D-arabinofuranoside Specification

The Thymine 1-beta-D-arabinofuranoside, with CAS registry number 605-23-2, has the systematic name of 1-(β-D-arabinofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione. And the chemical formula of this chemical is C₁₀H₁₄N₂O₆. This chemical should be stored at the temperature of 2-8°C. What's more, its EINECS is 210-083-7.

Physical properties of Thymine 1-beta-D-arabinofuranoside: (1)ACD/LogP: -1.02; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.02; (4)ACD/LogD (pH 7.4): -1.03; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 6.63; (8)ACD/KOC (pH 7.4): 6.51; (9)#H bond acceptors: 8; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 77.54 Å²; (13)Index of Refraction: 1.618; (14)Molar Refractivity: 57.43 cm³; (15)Molar Volume: 163.7 cm³; (16)Polarizability: 22.76×10^-24cm³; (17)Surface Tension: 75.9 dyne/cm.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C/1NC(=O)N(\C=C\1C)[C@@H]2O[C@@H]([C@@H](O)[C@@H]2O)CO
(2)InChI: InChI=1/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7+,9-/m1/s1
(3)InChIKey: DWRXFEITVBNRMK-JAGXHNFQBG
(4)Std. InChI: InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7+,9-/m1/s1
(5)Std. InChIKey: DWRXFEITVBNRMK-JAGXHNFQSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	> 10gm/kg (10000mg/kg)	Antimicrobial Agents and Chemotherapy. Vol. 17, Pg. 109, 1980.
mouse	LD50	intravenous	> 200mg/kg (200mg/kg)	Antimicrobial Agents and Chemotherapy. Vol. 17, Pg. 109, 1980.
mouse	LD50	oral	> 15gm/kg (15000mg/kg)	Antimicrobial Agents and Chemotherapy. Vol. 17, Pg. 109, 1980.
mouse	LD50	subcutaneous	7500mg/kg (7500mg/kg)	Antimicrobial Agents and Chemotherapy. Vol. 17, Pg. 109, 1980.

Product Name

THYMINE-BETA-D-ARABINOFURANOSIDE

Synthetic route

Thymine 1-beta-D-arabinofuranoside Specification

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