2,2'-Anhydro-5-methyluridine - CAS 22423-26-3

Name: 2,2'-Anhydro-5-methyluridine
Brand: BOC Sciences
Rating: 5 (1 reviews)

Catalog:	BB017599
Product Name:	2,2'-Anhydro-5-methyluridine
CAS:	22423-26-3
Synonyms:	O-2,2'-Anhydro-5-methyluridine; 2,2'-Anhydro-5-methyl-D-uridine; 2,2'-Anhydro-(1-b-D-arabinofuranosyl)-5-methyluracil; 2,2'-Anhydro-D-thymidine; 2,2'-Anhydro-5-methyluridine; (2R,3R,3aS,9aR)-3-Hydroxy-2-(hydroxymethyl)-7-methyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one; 2,2'-Anhydro-1-beta-arabinofuranosylthymine

Technical Data

IUPAC Name:	(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
Description:	2,2'-Anhydro-5-methyluridine is a chemically modified nucleoside derivative of uridine, where the 2' hydroxyl group of the ribose is linked to the 2-position of the uracil ring, forming an anhydro bond. Additionally, the uracil base is methylated at the 5-position. This modification alters the nucleoside's properties, making it useful in biochemical and pharmacological research, particularly in studies focused on nucleic acid chemistry and potential therapeutic applications.
Molecular Weight:	240.21
Molecular Formula:	C10H12N2O5
Canonical SMILES:	CC1=CN2C3C(C(C(O3)CO)O)OC2=NC1=O
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
InChI Key:	WLLOAUCNUMYOQI-JAGXHNFQSA-N
Boiling Point:	452.0±55.0 °C (Predicted)
Melting Point:	217.0-221.0 °C
Purity:	≥95%
Density:	1.88±0.1 g/cm³ (Predicted)
Appearance:	White to off-white crystalline powder
Storage:	Store at RT
LogP:	-1.43670

Publication Number	Title	Priority Date
WO-2021191830-A1	Methods and reagents for synthesizing nucleosides and analogues thereof	20200325
CN-110437292-A	A kind of preparation method for the thymidine that 2 '-O- replace	20190821
US-2020397790-A1	Uridine Phosphorylase (UPase) Inhibitors for Treatment of Liver Conditions	20190621
WO-2020257400-A1	Uridine phosphorylase (upase) inhibitors for treatment of liver conditions	20190621
WO-2020036974-A1	Methods and compositions for reducing radiation induced toxicity	20180814

PMID	Publication Date	Title	Journal
15698782	20050301	Synthesis and anti-viral activity of a series of d- and l-2'-deoxy-2'-fluororibonucleosides in the subgenomic HCV replicon system	Bioorganic & medicinal chemistry
16248042	20050101	Kilo-scale synthesis process for 2'-O-(2-methoxyethyl)-pyrimidine derivatives	Nucleosides, nucleotides & nucleic acids
11798305	20020125	Synthesis of 2'-O-[2-[(N,N-dimethylamino)oxy]ethyl] modified nucleosides and oligonucleotides	The Journal of organic chemistry
229223	19791001	Antiviral and antineoplastic activities of pyrimidine arabinosyl nucleosides and their 5'-amino derivatives	Journal of medicinal chemistry

Complexity:	432
Compound Is Canonicalized:	Yes
Covalently-Bonded Unit Count:	1
Defined Atom Stereocenter Count:	4
Defined Bond Stereocenter Count:	0
Exact Mass:	240.07462149
Formal Charge:	0
Heavy Atom Count:	17
Hydrogen Bond Acceptor Count:	5
Hydrogen Bond Donor Count:	2
Isotope Atom Count:	0
Monoisotopic Mass:	240.07462149
Rotatable Bond Count:	1
Topological Polar Surface Area:	91.6
Undefined Atom Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
XLogP3:	-2.1