2,2'-Anhydrouridine

Base Information

• Chemical Name: 2,2'-Anhydrouridine
• CAS No.: 3736-77-4
• Molecular Formula: C9H10N2O5
• Molecular Weight: 226.189
• Hs Code.: 29349990
• European Community (EC) Number: 223-107-6
• UNII: N9APX1AAR4
• DSSTox Substance ID: DTXSID801315535
• Nikkaji Number: J30.438G
• Wikidata: Q27095363
• Metabolomics Workbench ID: 149063
• ChEMBL ID: CHEMBL3251336
• Mol file: 3736-77-4.mol

Synonyms:0(2),2'-anhydrouridine;cyclouridine

Chemical Property of 2,2'-Anhydrouridine

Chemical Property:

• Melting Point: 239-240 °C
• Refractive Index: -20 ° (C=4, H2O)
• Boiling Point: 456.3 °C at 760 mmHg
• PKA: 12.55±0.40(Predicted)
• Flash Point: 229.8 °C
• PSA: 93.81000
• Density: 2.01 g/cm³
• LogP: -1.74510
• Storage Temp.: Store at RT.
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 226.05897142
• Heavy Atom Count: 16
• Complexity: 393

Purity/Quality:

99% ^*data from raw suppliers

O2,2''-Cyclouridine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN2C3C(C(C(O3)CO)O)OC2=NC1=O
• Isomeric SMILES: C1=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)OC2=NC1=O
• Description: 2,2'-Anhydro-1(B-D-arabinofuranosyl)uracil is a research tool for anticancer and antiviral studies. This works by inhibiting uridine phosphorylase, a key enzyme targeted by some antitumor drugs.
• Uses: O2,2''-Cyclouridine is a research tool for anticancer and antiviral studies. Research tool for antiviral and anticancer studies.1

Technology Process of 2,2'-Anhydrouridine

There total 65 articles about 2,2'-Anhydrouridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

bis(phenyl) carbonate (102-09-0) + uridine (58-96-8) → 2,2'-Anhydrouridine (3736-77-4)

Guidance literature:

bis(phenyl) carbonate; uridine; In N,N-dimethyl-formamide; at 80 ℃; for 1h; Inert atmosphere;

With sodium hydrogencarbonate; at 115 ℃; for 4h;

DOI:10.1080/15257770.2019.1646917

Reference yield: 94.0%

2',3'-O-sulfinyl uridine (51295-79-5) → 2,2'-Anhydrouridine (3736-77-4)

Guidance literature:

With sodium acetate; In N,N-dimethyl-formamide; at 85 ℃; for 4h;

DOI:10.1080/00397910600631924

Reference yield: 92.0%

uridine (58-96-8) → 2,2'-Anhydrouridine (3736-77-4)

Guidance literature:

With bis(phenyl) carbonate; sodium hydrogencarbonate; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 150 ℃; for 0.333333h;

DOI:10.1007/BF01165730

upstream raw materials:

O^5'-acetyl-2'-iodo-2'-deoxy-uridine

O^5'-acetyl-O^2'-(toluene-4-sulfonyl)-uridine

3’-O-benzoyl-2,2’-anhydro-1-(β-D-arabinofuranosyl)uracil

(3aS)-2t-acetoxymethyl-3c-benzoyloxy-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

Downstream raw materials:

araU

2'-S-(4-methoxyphenyl)-2'-thiouridine

1-(3',5'-di-O-trityl-β-D-arabinofuranosyl)uracil

2'-chloro-2'-deoxy-5'-O-trityluridine

Refernces

• 1、 Kang, Se Han,Oh, Seung Jun,Yoon, Mi Kyung,Ryu, Jin Sook,Lee, Won Koo,Choi, Sun Joo,Park, Kyung Pae,Moon, Dae Hyuk. "Simple and High radiochemical yield synthesis of 2'-Deoxy-2'-[18F]fluorouridine via a new nosylate precursor". . p. 1237 - 1246. Retrieved 2006.
• 2、 Miah, Anwar,Reese, Colin B.,Song, Quanlai. "2′,3′-Anhydrouridine". . p. 407 - 408. Retrieved 1997.
• 3、 Mudgal, Mukesh,Dang, Thao P.,Sobczak, Adam J.,Lumpuy, Daniel A.,Dutta, Priya,Ward, Samuel,Ward, Katherine,Alahmadi, Moaadh,Kumar, Anil,Sevilla, Michael D.,Wnuk, Stanislaw F.,Adhikary, Amitava. "Site of azido substitution in the sugar moiety of azidopyrimidine nucleosides influences the reactivity of aminyl radicals formed by dissociative electron attachment". . p. 11357 - 11370. Retrieved 2020/12/23.