2',3',5'-Tri-O-benzoyl-2-thiouridine

Base Information

• Chemical Name: 2',3',5'-Tri-O-benzoyl-2-thiouridine
• CAS No.: 21052-18-6
• Molecular Formula: C30H24N2O8S
• Molecular Weight: 572.595
• DSSTox Substance ID: DTXSID30550684
• Nikkaji Number: J2.267.099I
• Wikidata: Q82430111
• Mol file: 21052-18-6.mol

Synonyms:2',3',5'-Tri-O-benzoyl-2-thiouridine;21052-18-6;[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl benzoate;2-Thiouridine 2',3',5'-Tribenzoate;2-thiouridine tribenzoate;SCHEMBL11346599;DTXSID30550684;ZAHOZJCQNRXDIV-VNSJUHMKSA-N;2 inverted exclamation mark ,3 inverted exclamation mark ,5 inverted exclamation mark -Tri-O-benzoyl-2-thiouridine;J-013802;[(2R, 3R, 4R, 5R)-3, 4-dibenzoyloxy-5-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl benzoate;2-Sulfanylidene-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,3-dihydropyrimidin-4(1H)-one

Chemical Property of 2',3',5'-Tri-O-benzoyl-2-thiouridine

Chemical Property:

• PSA: 158.27000
• LogP: 4.52380
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 572.12533690
• Heavy Atom Count: 41
• Complexity: 1020

Purity/Quality:

97% ^*data from raw suppliers

2’,3’,5’-Tri-O-benzoyl-2-thiouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)N3C=CC(=O)NC3=S)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=S)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Uses: Protected 2-Thiouridine.

Technology Process of 2',3',5'-Tri-O-benzoyl-2-thiouridine

There total 10 articles about 2',3',5'-Tri-O-benzoyl-2-thiouridine 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: 89.0%

2-thiouracil (141-90-2,156-82-1) + 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (14215-97-5) → 2-thio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-(3H)pyrimidine-2,4-dione (21052-18-6)

Guidance literature:

2-thiouracil; With ammonium sulfate; chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; at 126 ℃; for 18h;

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose; With tin(IV) chloride; In 1,2-dichloro-ethane; at 20 ℃; for 1h;

Reference yield: 81.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine (32865-74-0) → 2-thio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-(3H)pyrimidine-2,4-dione (21052-18-6)

Guidance literature:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine; With tin(IV) chloride; In 1,2-dichloro-ethane; at 20 ℃; for 5h;

With sodium hydrogencarbonate; In 1,2-dichloro-ethane;

DOI:10.1021/jm060848j

Reference yield: 58.5%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 2-thiouracil (141-90-2,156-82-1) → 2-thio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-(3H)pyrimidine-2,4-dione (21052-18-6)

Guidance literature:

With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; tin(IV) chloride; In acetonitrile; at 24 ℃; for 6.5h;

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2-thiouracil

2',3',5'-tri-O-benzoyl-2,4-dithiouridine

4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine

Downstream raw materials:

2-(acetonyl)thio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyrimidinone

2-(2-oxobutyl)thio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyrimidinone

1-(2′,3′,5′-tri-O-benzoyl-β-D-ribofuranosyl)-4-pyrimidone

tribenzoyl uridine