1-beta-Arabinofuranosyl-5-(2-chlorovinyl)uracil

Base Information

• Chemical Name: 1-beta-Arabinofuranosyl-5-(2-chlorovinyl)uracil
• CAS No.: 77181-70-5
• Molecular Formula: C₁₁H₁₃ClN₂O₆
• Molecular Weight: 304.687
• UNII: 51A770XR7P
• DSSTox Substance ID: DTXSID00227937
• Nikkaji Number: J374.590B
• Wikidata: Q83107775
• Mol file: 77181-70-5.mol

Synonyms:1-beta-arabinofuranosyl-5-(2-chlorovinyl)uracil;CV-ara-U;CV-araU

Chemical Property of 1-beta-Arabinofuranosyl-5-(2-chlorovinyl)uracil

Chemical Property:

• PSA: 125.04000
• Density: 1.745g/cm³
• LogP: -1.23010
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 304.0462138
• Heavy Atom Count: 20
• Complexity: 480

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)C=CCl
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O)/C=C/Cl

Technology Process of 1-beta-Arabinofuranosyl-5-(2-chlorovinyl)uracil

There total 1 articles about 1-beta-Arabinofuranosyl-5-(2-chlorovinyl)uracil 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:

Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[5-((Z)-2-chloro-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester (132054-91-2,132988-00-2) → 1-(β-D-arabinofuranosyl)-5-[(E)-2-chlorovinyl]uracil (77181-70-5)

Guidance literature:

With methanol; ammonia; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)97919-X

Reference yield:

pyridine-3-carbonyl chloride hydrochloride (20260-53-1) + 1-(β-D-arabinofuranosyl)-5-[(E)-2-chlorovinyl]uracil (77181-70-5) → (E)-5-(2-chlorovinyl)-1-[5'-O-(pyridin-3-carboxyl)-β-D-arabinofuranosyl]uracil hydrochloride (946493-43-2)

Guidance literature:

pyridine-3-carbonyl chloride hydrochloride; 1-(β-D-arabinofuranosyl)-5-[(E)-2-chlorovinyl]uracil; With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

With hydrogenchloride; In methanol;

Reference yield:

4-(chlorocarbonyl)pyridine (14254-57-0) + 1-(β-D-arabinofuranosyl)-5-[(E)-2-chlorovinyl]uracil (77181-70-5) → (E)-5-(2-chlorovinyl)-1-[5'-O-(pyridin-4-carboxyl)-β-D-arabinofuranosyl]uracil hydrochloride (946493-44-3)

Guidance literature:

4-(chlorocarbonyl)pyridine; 1-(β-D-arabinofuranosyl)-5-[(E)-2-chlorovinyl]uracil; With triethylamine; In N,N-dimethyl-formamide;

With hydrogenchloride; In methanol;

upstream raw materials:

Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[5-((Z)-2-chloro-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester

Downstream raw materials:

(E)-5-(2-chlorovinyl)-1-[5'-O-(pyridin-3-carboxyl)-β-D-arabinofuranosyl]uracil hydrochloride

(E)-5-(2-chlorovinyl)-1-[5'-O-(pyridin-4-carboxyl)-β-D-arabinofuranosyl]uracil hydrochloride