5'-O-Benzoylthymidine

Base Information

• Chemical Name: 5'-O-Benzoylthymidine
• CAS No.: 35898-29-4
• Molecular Formula: C₁₇H₁₈N₂O₆
• Molecular Weight: 346.34
• DSSTox Substance ID: DTXSID30454057
• Nikkaji Number: J2.001.934D
• Wikidata: Q82275386
• Mol file: 35898-29-4.mol

Synonyms:5'-O-Benzoylthymidine;35898-29-4;((2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl benzoate;5 inverted exclamation mark -O-Benzoylthymidine;65475-51-6;benzoylthymidine;SCHEMBL4731692;DTXSID30454057;AMY30673;HY-154719;CS-0694482;F12802;5 inverted exclamation marka-O-benzoyl-thymidine

Chemical Property of 5'-O-Benzoylthymidine

Chemical Property:

• PSA: 110.88000
• LogP: 0.76270
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 346.11648630
• Heavy Atom Count: 25
• Complexity: 584

Purity/Quality:

97% ^*data from raw 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)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(=O)C3=CC=CC=C3)O

Technology Process of 5'-O-Benzoylthymidine

There total 15 articles about 5'-O-Benzoylthymidine 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: 98.0%

vinyl benzoate (769-78-8,24991-32-0) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5'-benzoylthymidine (35898-29-4,65475-51-6)

Guidance literature:

With Candida antarctica lipase B; In tetrahydrofuran; at 60 ℃; for 63h;

DOI:10.1016/j.tetlet.2003.12.098

Reference yield: 70.0%

(+/-)-thymidine (50-89-5,3424-98-4,4449-43-8,4781-17-3,16053-52-4,36646-86-3,39131-66-3,68224-82-8,128112-70-9,131682-41-2,137121-87-0,28854-96-8,3545-96-8,50-88-4) + benzoic acid (65-85-0,8013-63-6) → 5'-benzoylthymidine (35898-29-4,65475-51-6)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; In pyridine; for 5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85111-5

Reference yield: 60.0%

Acetone O-benzoyloxime (942-89-2) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5'-benzoylthymidine (35898-29-4,65475-51-6)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 48h; Candida antarctica lipase (SP₄₃₅A);

DOI:10.1021/jo00055a018

upstream raw materials:

(+/-)-thymidine

benzoic acid

Acetone O-benzoyloxime

thymidine

Downstream raw materials:

5'-O-benzoyl-3'-O-(methylthiomethyl)thymidine

5'-O-benzoyl-3'-O-methoxymethylthymidine

C₄₁H₃₉N₄O₁₃PS₂

Benzoic acid (2R,3S,5R)-3-(diisopropylamino-methoxy-phosphanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Refernces

• 1、 Sun, Huabing,Zheng, Liwei,Greenberg, Marc M.. "Independent Generation of Reactive Intermediates Leads to an Alternative Mechanism for Strand Damage Induced by Hole Transfer in Poly(dA-T) Sequences". supporting information. p. 11308 - 11316. Retrieved 2018/09/13.
• 2、 Rodriguez-Perez, Tatiana,Fernandez, Susana,Martinez-Montero, Saul,Gonzalez-Garcia, Tania,Sanghvi, Yogesh S.,Gotor, Vicente,Ferrero, Miguel. "Chemoenzymatic synthesis of 3′-O-acetal-protected 2′-deoxynucleosides as building blocks for nucleic acid chemistry". experimental part. p. 1736 - 1744. Retrieved 2010/06/13.