2,2'-Anhydro-1-beta-arabinofuranosylthymine

HCID 168045

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Basic information

CAS: 22423-26-3
Standard SMILES: Cc1cn2c(nc1=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]12
InChIKey: WLLOAUCNUMYOQI-JAGXHNFQSA-N
Molecular formula: C10H12N2O5
Average molar mass: 240.21 g/mol
Monoisotopic mass: 240.07462149

Names & identifiers

Preferred name: 2,2'-Anhydro-1-beta-arabinofuranosylthymine
IUPAC: (2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-11-methyl-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one
English name: 2,2'-Anhydro-5-methyluridine
Molecular formula: C10H12N2O5
Molecular weight: 240.21

Names & synonyms

22423-26-32,2'-Anhydro-athy2,2'-Anhydro-11-beta-D-arabinofuranosylthymine2,2'-Anhydro-1-beta-arabinofuranosylthymine6H-Furo(2',3':4,5)oxazolo(3,2-a)pyrimidin-6-one, 2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-, (2R-(2alpha,3beta,3abeta,9abeta))-RefChem:3976112,2'-Anhydro-5-methyluridineGQZ99GWR3T(2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-11-methyl-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-oneTK-112690(2R,3R,3aS,9aR)-3-Hydroxy-2-(hydroxymethyl)-7-methyl-3,3a-dihydro-2H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6(9aH)-oneAKOS015918519

Show more names

O-2,2'-cyclo-5-methyluridine2,2`-CyclothyMidine2,2'-Anhydro-5-Me-U2,2'-Anhydro-5-methy2,2'-Anhydrothimidine5-Me-2, 2'-Anhydro-rUL-2,2'-AnhydrothyMidine

6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one,2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-,(2R,3R,3aS,9aR)-2,2'-O-Anhydro-5-methyluridineMFCD002335552,2'-AnhydrothymidineF121666H-FURO(2',3':4,5)OXAZOLO(3,2-A)PYRIMIDIN-6-ONE, 2,3,3A,9A-TETRAHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-7-METHYL-, (2R,3R,3AS,9AR)-6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one, 2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-, (2R,3R,3aS,9aR)-2,2-Anhydrothymidine

Database identifiers

CAS: 22423-26-3
PubChem CID: 168045
DTXSID: DTXSID90945097
ChEMBL: CHEMBL3251296
UNII: GQZ99GWR3T
EC Number: 898-613-9
Nikkaji: J144.841B

Properties

Computed structural properties

XLogP: -2.1
Topological polar surface area: 91.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 1
Heavy atoms: 17
Formal charge: 0
Complexity: 432

Physicochemical properties

Melting point: 217 to · 217.0 to 221.0 °C
Boiling point: 452 · 452.0±55.0 °C(Predicted)
Density: 1.88 · 1.88±0.1 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
Water Solubility: Soluble in water
form: powder to crystal
pka: 12.56 · 12.56±0.60(Predicted)
color: White to Almost white
InChI: InChI=1S/C10H12N2O5/c1-4-2-12-9-7(6(14)5(3-13)16-9)17-10(12)11-8(4)15/h2,5-7,9,13-14H,3H2,1H3/t5-,6-,7+,9-/m1/s1
InChIKey: WLLOAUCNUMYOQI-JAGXHNFQSA-N
SMILES: C12O[C@@]3([H])[C@H](O)[C@@H](CO)O[C@@]3([H])N1C=C(C)C(=O)N=2
CAS DataBase Reference: 22423 · 22423-26-3(CAS DataBase Reference)
FDA UNII: 99 GWR3T · GQZ99GWR3T
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
HS Code: 2940 · 2940.00.6000

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (100%)

Safety data

hs_code: 2940.00.6000
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications

Uses2,2'-Anhydro-5-methyluridine serves as a precursor to synthesize 5'-O-(4,4'-dimethoxytrityl)-2,2'-anhydro thymidine by reaction with 4,4'-dimethoxytrityl chloride in anhydrous pyridine[6].