A4044
2,3′-Anhydrothymidine
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About This Item
Empirical Formula (Hill Notation):
C10H12N2O4
CAS Number:
Molecular Weight:
224.21
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
Assay:
≥97% (TLC)
Form:
powder
Solubility:
methanol: 50 mg/mL, clear, colorless to faintly yellow
Storage temp.:
−20°C
SMILES string
CC1=C[N@@H]2[C@H]3C[C@@H](OC2=NC1=O)[C@@H](CO)O3
InChI
1S/C10H12N2O4/c1-5-3-12-8-2-6(7(4-13)15-8)16-10(12)11-9(5)14/h3,6-8,13H,2,4H2,1H3/t6-,7-,8-/m1/s1
InChI key
JCSNHEYOIASGKU-BWZBUEFSSA-N
assay
≥97% (TLC)
form
powder
solubility
methanol: 50 mg/mL, clear, colorless to faintly yellow
storage temp.
−20°C
Quality Level
Application
2,3′-Anhydrothymidine may be derivitized to 5′-benzoyl-2′,3′-anhydrothymidine for use in the synthesis of 5′-Derivatives of 3′-(tetrazole-2′-yl)-3′-deoxythymidines. 2,3′-Anhydrothymidine may be contacted with thioacetic acid to produce 3′-S-acetyl-3′-thio-2′-deoxynucleosides.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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V A Ostrovskiĭ et al.
Bioorganicheskaia khimiia, 21(1), 49-54 (1995-01-01)
5''-Derivatives of 3'-(tetrazole-2''-yl)-3'-deoxythymidines were synthesized by interaction of 5'-benzoyl-2',3'-anhydrothymidine with tetrazole or its 5-derivatives followed by debenzoylation. Structures of two of them, 3'-(tetrazole-2''-yl)-3'-deoxythymidine and 3'-(5''-methyltetrazole-2''-yl)-3'-deoxythymidine, elucidated by X-ray analysis, revealed anti conformation of thymine about the glycosidic bond and 2'-endo-3'-exo-conformation
Peihua Shang et al.
Nucleosides, nucleotides & nucleic acids, 27(12), 1272-1281 (2008-11-13)
A general method is described for synthesizing 3',5'-dithio-2'-deoxypyrimidine nucleosides 6 and 13 from normal 2'-deoxynucleosides. 2,3'-Anhydronucleosides 2 and 9 are applied as intermediates in the process to reverse the conformation of 3'-position on sugar rings. The intramolecular rings of 2,3'-anhydrothymidine
Maren Schulze et al.
Methods in molecular biology (Clifton, N.J.), 329, 45-58 (2006-07-19)
The in vitro differentiation of mouse embryonic stem (ES) cells into different somatic cell types such as neurons, endothelial cells, or myocytes is well established, and many mouse ES cell lines have been created so far. The establishment of rat
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