1beta-D-Arabinofuranosyl-5-methylcytosine

Base Information

• Chemical Name: 1beta-D-Arabinofuranosyl-5-methylcytosine
• CAS No.: 6829-31-8
• Molecular Formula: C₁₀H₁₅N₃O₅
• Molecular Weight: 257.246
• DSSTox Substance ID: DTXSID101016978
• Mol file: 6829-31-8.mol

Synonyms:1 beta-D-arabinofuranosyl-5-methylcytosine;5-methyl ara-C;5-methylarabinosylcytosine

Chemical Property of 1beta-D-Arabinofuranosyl-5-methylcytosine

Chemical Property:

• Vapor Pressure: 8.5E-14mmHg at 25°C
• Boiling Point: 537.5°Cat760mmHg
• Flash Point: 278.9°C
• Density: 1.79g/cm³
• XLogP3: -2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 257.10117059
• Heavy Atom Count: 18
• Complexity: 422

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: CC1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O

Technology Process of 1beta-D-Arabinofuranosyl-5-methylcytosine

There total 5 articles about 1beta-D-Arabinofuranosyl-5-methylcytosine 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:

2,4-diethoxy-5-methylpyrimidine (7193-87-5) + 1,2,3,5-tetraacetylribose (13035-61-5) → 4-amino-5-methyl-1-α-D-ribofuranosyl-1H-pyrimidin-2-one (2140-61-6,6829-31-8,18492-10-9,83610-78-0,98178-53-1)

Guidance literature:

With hydrogen bromide; benzene; beim Erwaermen <5 d> des Reaktionsprodukts mit methanol. NH3;

DOI:10.1021/ja01123a026

Reference yield:

1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-ethoxy-5-methyl-1H-pyrimidin-2-one (119410-86-5) → 1-(β-D-Arabinofuranosyl)-5-methyl-cytosin (6829-31-8)

Guidance literature:

With ammonia; In methanol; at 100 ℃; for 48h;

DOI:10.1016/S0040-4039(00)88789-4

Reference yield:

1-<2,3,5-Tris-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>-4-ethoxy-2-pyrimidone (129436-34-6) → 1-(β-D-Arabinofuranosyl)-5-methyl-cytosin (6829-31-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, -80 deg C, 5 min

3: NH₃ / methanol / 48 h / 100 °C

With ammonia; lithium diisopropyl amide; In methanol;

DOI:10.1016/S0040-4039(00)88789-4

upstream raw materials:

2,4-diethoxy-5-methylpyrimidine

1,2,3,5-tetraacetylribose

1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-ethoxy-5-methyl-1H-pyrimidin-2-one

1-<2,3,5-Tris-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>-4-ethoxy-2-pyrimidone