L-Thymidine

Base Information

• Chemical Name: L-Thymidine
• CAS No.: 16053-52-4
• Molecular Formula: C10H14 N2 O5
• Molecular Weight: 242.232
• NSC Number: 526738,21548
• DSSTox Substance ID: DTXSID20936337
• Nikkaji Number: J2.569.651D
• Wikidata: Q82912533
• ChEMBL ID: CHEMBL6497
• Mol file: 16053-52-4.mol

Synonyms:1-(2'-deoxy-beta-D-threo-pentofuranosyl)thymine;1-(2'-deoxy-beta-threopentofuranosyl)thymine;1-DPFT

Chemical Property of L-Thymidine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 104.55000
• Density: 1.452g/cm³
• LogP: -1.51430
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 242.09027155
• Heavy Atom Count: 17
• Complexity: 381

Purity/Quality:

97% ^*data from raw suppliers

3’-β-Thymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Physical/Radiation -> Radioactive Compounds
• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
• Uses: 3’-β-Thymidine (Stavudine EP Impurity B) is an intermediate in the production of fluorothymidine and phosphorylase derivatives (1,2). Stavudine is used as an antiviral agent. Reverse transcriptase inhibitor (3).

Technology Process of L-Thymidine

There total 63 articles about L-Thymidine 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%

1-(2-deoxy-3,5-di-p-toluoyl-β-L-ribose)-5-methyluracil (3056-13-1) → C10H14N2O5 (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)

Guidance literature:

With methanol; sodium methylate; at 45 - 50 ℃;

Reference yield: 93.4%

3',5'-di-O-acetyl-β-L-thymidine (433733-94-9) → C10H14N2O5 (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)

Guidance literature:

With ammonia; In methanol; at 6 ℃; for 72h;

Reference yield: 90.0%

3',5'-di-O-levulinoyl-β-L-thymidine (793716-98-0) → C10H14N2O5 (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) + 3'-O-levulinoyl-β-L-thymidine

Guidance literature:

With Candida antarctica lipase B; phosphate buffer; In 1,4-dioxane; at 30 ℃; for 28.5h; pH=7;

DOI:10.1021/ol048502v

upstream raw materials:

2',3',5'-tri-O-benzoyl-5-methyl-L-uridine

3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-L-thymidine

3',5'-di-O-levulinoyl-β-L-thymidine

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

Downstream raw materials:

S-methyl-L-cysteine

3-methylthymidine

5'-(2,6-dichlorobenzoyl)-deoxythymidine

5'-benzoylthymidine

Refernces

• 1、 Brickute,Beckley,Allott,Braga,Barnes,Thorley,Aboagye. "Synthesis and evaluation of 3′-[18F]fluorothymidine-5′-squaryl as a bioisostere of 3′-[18F]fluorothymidine-5′-monophosphate". . p. 12423 - 12433. Retrieved 2021/04/07.
• 2、 -. "Synthesis method of beta-thymidine". . . Retrieved 2017/08/14.