((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl acetate

Base Information

• Chemical Name: ((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl acetate
• CAS No.: 42867-74-3
• Molecular Formula: C11H12N2O5
• Molecular Weight: 252.227
• DSSTox Substance ID: DTXSID30472933
• Nikkaji Number: J784.407G
• Wikidata: Q82302123
• Mol file: 42867-74-3.mol

Synonyms:42867-74-3;((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl acetate;[(2S,5R)-5-(2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl acetate;5 inverted exclamation mark -O-Acetyl-2 inverted exclamation mark ,3 inverted exclamation mark -dideoxy-2 inverted exclamation mark ,3 inverted exclamation mark -didehydro-uridine;SCHEMBL1879258;DTXSID30472933;ZJEYZGAQPYLRFC-WCBMZHEXSA-N;AKOS024259263;HY-154542;CS-0676384;5'-O-acetyl-2',3'-didehydro-2',3'-dideoxyuridine;((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methylacetate;[(2S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl acetate

Chemical Property of ((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl acetate

Chemical Property:

• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 252.07462149
• Heavy Atom Count: 18
• Complexity: 443

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C=CC(O1)N2C=CC(=O)NC2=O
• Isomeric SMILES: CC(=O)OC[C@@H]1C=C[C@@H](O1)N2C=CC(=O)NC2=O

Technology Process of ((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl acetate

There total 1 articles about ((2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl acetate 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: 65.0%

acetic anhydride (108-24-7) + 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)uracil (116597-18-3) → 2,2''-anhydro-1-(3'',5''-di-O-acetyl-β-D-arabinofuranosyl)uracil (28309-53-7) + 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-uracil (42867-74-3)

Guidance literature:

for 5h; Reflux;

DOI:10.1107/S0108270113000395

Reference yield: 43.0%

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-uracil (42867-74-3) → uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 2',3'-dideoxy-2',3'-didehydrouridine (5974-93-6)

Guidance literature:

With ammonium hydroxide; In methanol; for 12h; Ambient temperature;

DOI:10.1021/jo00256a056

Reference yield:

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-uracil (42867-74-3) → 2',3'-Dideoxyuridine (5983-09-5,153547-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / 29percent NH₄OH / methanol / 12 h / Ambient temperature

2: 97 percent / H₂ / 5percent Pd/C / methanol / 1 h

With ammonium hydroxide; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00256a056

upstream raw materials:

acetic anhydride

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)uracil

Downstream raw materials:

uracil

2',3'-dideoxy-2',3'-didehydrouridine

1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-iodo-uracil

1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-fluorouracil