5-Hydroxymethyldeoxycytidylic acid

Base Information

• Chemical Name: 5-Hydroxymethyldeoxycytidylic acid
• CAS No.: 13009-95-5
• Molecular Formula: C10H16 N3 O8 P
• Molecular Weight: 337.226
• DSSTox Substance ID: DTXSID40156333
• Nikkaji Number: J2.745.326K
• Wikidata: Q27102149
• Metabolomics Workbench ID: 50714
• Mol file: 13009-95-5.mol

Synonyms:5-HMDCyt;5-hydroxymethyldeoxycytidylate;5-hydroxymethyldeoxycytidylic acid;5-hydroxymethyldeoxycytidylic acid, (2-)-ion

Chemical Property of 5-Hydroxymethyldeoxycytidylic acid

Chemical Property:

• Vapor Pressure: 8.05E-23mmHg at 25°C
• Boiling Point: 702.6°Cat760mmHg
• Flash Point: 378.7°C
• PSA: 187.17000
• Density: 2.03g/cm³
• LogP: -1.34330
• XLogP3: -3.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 337.06750147
• Heavy Atom Count: 22
• Complexity: 558

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)CO)COP(=O)(O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)CO)COP(=O)(O)O)O

Technology Process of 5-Hydroxymethyldeoxycytidylic acid

There total 9 articles about 5-Hydroxymethyldeoxycytidylic acid 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:

5-methyl-2′-deoxycytidine 5′-monophosphate (2498-41-1) → 5-hydroxymethyl-2'-deoxycytidine 5'-monophosphate (13009-95-5) + 5-formyl-2'-deoxycytidine 5'-monophosphate (137017-46-0)

Guidance literature:

With sodium persulfate; In water; at 75 ℃; for 3h; sodium phosphate buffer pH 7.0;

DOI:10.1246/cl.1991.1591

Reference yield:

C12H18N3O9P → 5-hydroxymethyl-2'-deoxycytidine 5'-monophosphate (13009-95-5)

Guidance literature:

With water; potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1039/c4ra07670b

Reference yield:

5-acetoxymethyl-3',5'-di-O-tert-butyldimethylsilyl-2'-deoxycytidine (354581-54-7) → 5-hydroxymethyl-2'-deoxycytidine 5'-monophosphate (13009-95-5)

Guidance literature:

Multi-step reaction with 3 steps

1: trichlorophosphate; trimethyl phosphite / 2 h / 0 °C

2: trifluoroacetic acid / water / 1 h / 20 °C

3: potassium carbonate; water / methanol / 1 h / 20 °C

With trimethyl phosphite; water; potassium carbonate; trifluoroacetic acid; trichlorophosphate; In methanol; water;

DOI:10.1039/c4ra07670b

upstream raw materials:

formaldehyd

cytidine 5'-(dihydrogen phosphate)

5-methyl-2′-deoxycytidine 5′-monophosphate

5-acetoxymethyl-3',5'-di-O-tert-butyldimethylsilyl-2'-deoxycytidine

Refernces

• 1、 Itahara,Yoshitake,Koga,Nishino. "Oxidation of nucleic acid related compounds by the peroxodisulfate ion". . p. 2257 - 2264. Retrieved 2007/10/02.
• 2、 Alegria. "Hydroxymethylation of pyrimidine mononucleotides with formaldehyde.". . p. 317 - 324. Retrieved 2007/10/04.