[5-(4-Benzamido-2-oxopyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate

Base Information

• Chemical Name: [5-(4-Benzamido-2-oxopyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS No.: 23624-64-8
• Molecular Formula: C37H29 N3 O9
• Molecular Weight: 659.652
• NSC Number: 95000
• DSSTox Substance ID: DTXSID30946442
• Mol file: 23624-64-8.mol

Synonyms:23624-64-8;NSC95000;DTXSID30946442;NSC-95000;4-(Benzoylimino)-1-(2,3,5-tri-O-benzoylpentofuranosyl)-1,4-dihydropyrimidin-2-ol

Chemical Property of [5-(4-Benzamido-2-oxopyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.35g/cm³
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 13
• Exact Mass: 659.19037951
• Heavy Atom Count: 49
• Complexity: 1260

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC2=NC(=O)N(C=C2)C3C(C(C(O3)COC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6

Technology Process of [5-(4-Benzamido-2-oxopyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate

There total 16 articles about [5-(4-Benzamido-2-oxopyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate 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: 100.0%

p-tolyl 2,3,5-tri-O-benzoyl-1-thio-β-D-ribofuranoside (918800-27-8) + N4,O-bis(trimethylsilyl)-N4-benzoylcytosine (64339-87-3) → N4-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine (23624-64-8)

Guidance literature:

p-tolyl 2,3,5-tri-O-benzoyl-1-thio-β-D-ribofuranoside; With trifluoromethylsulfonic anhydride; di(p-tolyl) sulfoxide; In dichloromethane; at -70 - -40 ℃; for 0.833333h; Molecular sieve;

N₄,O-bis(trimethylsilyl)-N₄-benzoylcytosine; In dichloromethane; acetonitrile; at -70 - -20 ℃; for 4h; stereoselective reaction;

DOI:10.1039/c5cc03617h

Reference yield: 96.0%

→ N4-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine (23624-64-8)

Guidance literature:

With N,O-Bis(trimethylsilyl)trifluoroacetamide; In acetonitrile; at 50 ℃; for 0.5h; Inert atmosphere;

In acetonitrile; at 20 ℃; for 0.666667h; Inert atmosphere; Molecular sieve;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 20 ℃; for 3h; Inert atmosphere; Molecular sieve;

Reference yield: 95.0%

4-N-benzoylcytosine (26661-13-2) + 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl ortho-hexynylbenzoate → N4-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine (23624-64-8)

Guidance literature:

4-N-benzoylcytosine; 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl ortho-hexynylbenzoate; With N,O-Bis(trimethylsilyl)trifluoroacetamide; In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); In acetonitrile; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201100514

upstream raw materials:

benzoyl chloride

CYTIDINE

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl methyl carbonate

Downstream raw materials:

CYTIDINE

tribenzoyl uridine

5,6-dihydro-N⁴-hydroxy-6-hydroxyamino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)cytosine

2',3',5'-tri-O-benzoyl-L-cytidine