Thymidine 3',5'-dibenzoate

Base Information

• Chemical Name: Thymidine 3',5'-dibenzoate
• CAS No.: 35898-30-7
• Molecular Formula: C24H22N2O7
• Molecular Weight: 450.448
• European Community (EC) Number: 252-786-1
• DSSTox Substance ID: DTXSID10189456
• Nikkaji Number: J319.560K
• Wikidata: Q83061554
• Mol file: 35898-30-7.mol

Synonyms:35898-30-7;3',5'-Di-O-benzoylthymidine;Thymidine 3',5'-dibenzoate;[(2R,3S,5R)-3-benzoyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate;((2R,3S,5R)-3-(benzoyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl benzoate;3',5'-di-O-benzoyl thymidine;EINECS 252-786-1;starbld0016808;SCHEMBL10664373;DTXSID10189456;SNKWLBSAKXIYKF-XUVXKRRUSA-N;AKOS037489105;NS00029943;A823028;[(2R,3S,5R)-3-benzoyloxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl benzoate

Chemical Property of Thymidine 3',5'-dibenzoate

Chemical Property:

• PSA: 116.69000
• Density: 1.39 g/cm³
• LogP: 2.21510
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 450.14270105
• Heavy Atom Count: 33
• Complexity: 799

Purity/Quality:

97% ^*data from raw suppliers

3',5'-DI-OXO-BENZOYLTHYMIDINE 99.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)COC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4

Technology Process of Thymidine 3',5'-dibenzoate

There total 23 articles about Thymidine 3',5'-dibenzoate 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: 95.0%

benzoyl chloride (98-88-4) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 3',5'-di-O-benzoylthymidine (35898-30-7)

Guidance literature:

With pyridine; at 50 - 55 ℃; for 72h;

DOI:10.1248/cpb.43.144

Reference yield: 94.0%

benzoyl cyanide (613-90-1) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 3',5'-di-O-benzoylthymidine (35898-30-7)

Guidance literature:

With pyridine; dmap; at 40 ℃; for 5h;

DOI:10.1081/SCC-200051693

Reference yield: 93.0%

benzoic acid anhydride (93-97-0) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 3',5'-di-O-benzoylthymidine (35898-30-7)

Guidance literature:

With dmap; In various solvent(s); at 50 ℃; for 2h;

DOI:10.1016/j.tetlet.2006.11.155

upstream raw materials:

benzoyl chloride

thymidine

C₂₃H₂₉N₂O₇P

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

Downstream raw materials:

thymidine

5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

O^3'_,O5'-dibenzoyl-N⁴-hydroxy-5-methyl-2'-deoxy-cytidine

N,5-dimethyl-2’-deoxycytidine

Refernces

• 1、 Kodr, David,Yenice, Cansu Pinar,Simonova, Anna,Safti?, Dijana Pavlovi?,Pohl, Radek,Sykorová, Veronika,Ortiz, Mayreli,Havran, Luděk,Fojta, Miroslav,Lesnikowski, Zbigniew J.,O'Sullivan, Ciara K.,Hocek, Michal. "Carborane- or Metallacarborane-Linked Nucleotides for Redox Labeling. Orthogonal Multipotential Coding of all Four DNA Bases for Electrochemical Analysis and Sequencing". . p. 7124 - 7134. Retrieved 2021.
• 2、 Shen, Bo,Jamison, Timothy F.. "Continuous flow photochemistry for the rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides". . p. 157 - 164. Retrieved 2013/04/10.