5-Hydroxy-2'-deoxycytidine

Base Information

• Chemical Name: 5-Hydroxy-2'-deoxycytidine
• CAS No.: 52278-77-0
• Molecular Formula: C9H13 N3 O5
• Molecular Weight: 243.219
• UNII: 6JHE7FC4BX
• DSSTox Substance ID: DTXSID00966652
• Nikkaji Number: J740.951F
• Wikidata: Q27265006
• ChEMBL ID: CHEMBL217849
• Mol file: 52278-77-0.mol

Synonyms:5-hydroxy-2'-deoxycytidine;oh-5-dC

Chemical Property of 5-Hydroxy-2'-deoxycytidine

Chemical Property:

• Boiling Point: 536.1°Cat760mmHg
• Flash Point: 278°C
• PSA: 130.83000
• Density: 1.89g/cm³
• LogP: -1.24700
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 243.08552052
• Heavy Atom Count: 17
• Complexity: 394

Purity/Quality:

97% ^*data from raw suppliers

5-Hydroxy-2’-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)O)CO)O
• Uses: 5-Hydroxy-2’-deoxycytidine have been used as a substrate for uracil DNA N-glycosylase and has been used to study the oxidation of DNA due to exposure to reactive oxygen species.

Technology Process of 5-Hydroxy-2'-deoxycytidine

There total 1 articles about 5-Hydroxy-2'-deoxycytidine 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:

2'-Deoxycytidine (951-77-9) → 5-bromo-2'-deoxycytidine (1022-79-3) + 5-Hydroxy-2'-deoxycytidine (52278-77-0)

Guidance literature:

With ammonium bromide; peroxynitrite; In phosphate buffer; at 37 ℃; for 5h; pH=7.4;

DOI:10.1016/j.bmc.2008.03.007

Reference yield:

5-Hydroxy-2'-deoxycytidine (52278-77-0) → 3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5,6,7,8-tetrafluoro-3H,9H-10-oxa-1,3,9-triaza-anthracen-2-one (218145-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / K₂CO₃ / dimethylsulfoxide / 50 °C

2: 52 percent / pyridine / Ambient temperature

With pyridine; potassium carbonate; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)01932-7

Reference yield:

5-Hydroxy-2'-deoxycytidine (52278-77-0) → C36H30F4N3O9P*C6H15N

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / K₂CO₃ / dimethylsulfoxide / 50 °C

2: 52 percent / pyridine / Ambient temperature

3: 80 percent / 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one, pyridine / CH₂Cl₂ / 0 deg C up to RT

With pyridine; 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one; potassium carbonate; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)01932-7

upstream raw materials:

2'-Deoxycytidine

Downstream raw materials:

5-hydroxycytosine

3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5,6,7,8-tetrafluoro-3H,9H-10-oxa-1,3,9-triaza-anthracen-2-one

Benzoic acid 4-benzoylamino-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl ester

Benzoic acid 4-benzoylamino-2-oxo-1-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1,2-dihydro-pyrimidin-5-yl ester

Refernces