4-amino-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one

Base Information

• Chemical Name: 4-amino-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
• CAS No.: 838-07-3
• Molecular Formula: C10H15N3O4
• Molecular Weight: 241.247
• Hs Code.: 29389090
• RXCUI: 2642190
• Metabolomics Workbench ID: 38085
• Mol file: 838-07-3.mol

Synonyms:5-methyl-2'-deoxycytidine;5-methyldeoxycytidine

Chemical Property of 4-amino-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 217-219 °C(lit.)
• Refractive Index: 44 ° (C=1.4, H2O)
• Boiling Point: 492.8 °C at 760 mmHg
• PKA: pK1:4.33 (25°C)
• Flash Point: 251.9 °C
• PSA: 110.60000
• Density: 1.64 g/cm³
• LogP: -0.64420
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly)
• Water Solubility.: Soluble in water.
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 241.10625597
• Heavy Atom Count: 17
• Complexity: 393

Purity/Quality:

99% ^*data from raw suppliers

5-Methyldeoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)N=C1N)C2CC(C(O2)CO)O
• Isomeric SMILES: CC1=CN(C(=O)N=C1N)[C@H]2CC([C@H](O2)CO)O
• Description: 5-Methyl-2'-deoxycytidine is a nucleoside analogue that inhibits the synthesis of DNA. 5-Methyl-2'-deoxycytidine prevents methylation of guanine, which disrupts the binding of guanine nucleotide-binding proteins to the dna template and prevents polymerase chain reactions. 2'-Deoxy-5-methylcytidine is also a methyltransferase inhibitor, which means it blocks the enzyme responsible for adding methyl groups to cytosine molecules.
• Uses: 5-Methyl-2'-deoxycytidine is a pyrimidine nucleoside that when incorporated into single-stranded DNA can act in cis to signal de novo DNA methylation. It has been used in epigenetics research to investigate the dynamics of DNA methylation pattern in the control of gene expression. 5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation. A Cytidine (C998300) analog and also an isostere of Thymidine (T412000).

Technology Process of 4-amino-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one

There total 21 articles about 4-amino-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one 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: 92.0%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5-methyldeoxycytidine (838-07-3)

Guidance literature:

thymidine; With 1,8-diazabicyclo[5.4.0]undec-7-ene; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In N,N-dimethyl-formamide; at 20 ℃; for 0.0166667h;

With ammonium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Reagent/catalyst; Time;

DOI:10.1016/j.tet.2018.10.046

Reference yield: 88.0%

3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-5-methylcytidine (80991-42-0) → 5-methyldeoxycytidine (838-07-3)

Guidance literature:

With pyridine; pyridine hydrofluoride; In ethyl acetate;

DOI:10.1002/anie.201002033

Reference yield: 85.0%

5-methyl-1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)cytidine (115652-25-0) → 5-methyldeoxycytidine (838-07-3)

Guidance literature:

With ammonia; at 25 ℃;

DOI:10.1016/0040-4020(96)00289-X

upstream raw materials:

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

O^3'_,O5'-dibenzoyl-4-thio-thymidine

1-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone

thymidine

Downstream raw materials:

thymidine

5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-deoxy-N⁴-benzoyl-5-methylcytidine

3'-(diisopropylamino-cyanoethoxyphosphino)-5'-(4,4'-dimethoxytrityl)-4-N-benzoyl-5-formyl-2'deoxycytidine

4-N-benzoyl-5-formyl-2'deoxycytidine

Refernces

• 1、 Kawai, Kazuaki,Li, Yun-Shan,Song, Ming-Fen,Kasai, Hiroshi. "DNA methylation by dimethyl sulfoxide and methionine sulfoxide triggered by hydroxyl radical and implications for epigenetic modifications". . p. 260 - 265. Retrieved 2010.
• 2、 Muenzel, Martin,Globisch, Daniel,Brueckl, Tobias,Wagner, Mirko,Welzmiller, Veronika,Michalakis, Stylianos,Mueller, Markus,Biel, Martin,Carell, Thomas. "Quantification of the sixth DNA base hydroxymethylcytosine in the brain". supporting information; experimental part. p. 5375 - 5377. Retrieved 2010/10/18.