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Thymine 1-beta-D-arabinofuranoside
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Name

Thymine 1-beta-D-arabinofuranoside

 EINECS 210-083-7
CAS No. 605-23-2 Density 1.576g/cm3
PSA 124.78000 LogP -2.54350
Solubility N/A Melting Point N/A
Formula C10H14N2O6 Boiling Point N/A
Molecular Weight 258.231 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 605-23-2 (THYMINE-BETA-D-ARABINOFURANOSIDE) Hazard Symbols N/A
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;

Article Data 20

Thymine 1-beta-D-arabinofuranoside Synthetic route

22423-26-3

O-2,2'-cyclo-5-methyluridine

605-23-2

thymine arabinoside

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium hydroxide In 1,4-dioxane; water at 20℃; for 0.333333h; Hydrolysis; Alkaline hydrolysis;A 65%
B 25%
C n/a
1463-10-1

5-Methyluridine

605-23-2

thymine arabinoside

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

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) Effect 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.

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