3'-deoxy-3'-iodo-5'-O-tritylthymidine

Base Information

• Chemical Name: 3'-deoxy-3'-iodo-5'-O-tritylthymidine
• CAS No.: 25442-44-8
• Molecular Formula: C29H27IN2O4
• Molecular Weight: 594.449
• DSSTox Substance ID: DTXSID70455260
• Nikkaji Number: J790.093G
• Wikidata: Q82277184
• Mol file: 25442-44-8.mol

Synonyms:3'-deoxy-3'-iodo-5'-O-tritylthymidine;25442-44-8;SCHEMBL6328988;DTXSID70455260;SUVZWOWKXHLILJ-JIMJEQGWSA-N;3'-Iodo-5'-O-trityl-3'-deoxythymidine

Chemical Property of 3'-deoxy-3'-iodo-5'-O-tritylthymidine

Chemical Property:

• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 594.10155
• Heavy Atom Count: 36
• Complexity: 769

Purity/Quality:

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(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)I
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)I

Technology Process of 3'-deoxy-3'-iodo-5'-O-tritylthymidine

There total 8 articles about 3'-deoxy-3'-iodo-5'-O-tritylthymidine 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: 68.0%

5'-O-tritylthymidine (7791-71-1) → 1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine (25442-44-8)

Guidance literature:

With methyltriphenoxyphosphonium iodide; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79047-2

Reference yield:

trityl chloride (76-83-5) → 1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine (25442-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / pyridine / 1 h / Heating

2: 68 percent / (PhO)3MeP⁺I^- / dimethylformamide / 16 h / Ambient temperature

With pyridine; methyltriphenoxyphosphonium iodide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79047-2

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine (25442-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / pyridine / 1 h / Heating

2: 68 percent / (PhO)3MeP⁺I^- / dimethylformamide / 16 h / Ambient temperature

With pyridine; methyltriphenoxyphosphonium iodide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79047-2

upstream raw materials:

5'-O-tritylthymidine

trityl chloride

thymidine

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

Downstream raw materials:

3'-deoxy-3'-iodothymidine

1-(3'-C-cyano-2',3'-dideoxy-β-D-erythro-pentofuranosyl)thymine

3'-O-triphenylmethylthymidine

Acetic acid (2S,3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-ylmethyl ester

Refernces

• 1、 Shakya, Neeraj,Srivastav, Naveen C.,Desroches, Nancy,Agrawal, Babita,Kunimoto, Dennis Y.,Kumar, Rakesh. "3′-Bromo analogues of pyrimidine nucleosides as a new class of potent inhibitors of mycobacterium tuberculosis". experimental part. p. 4130 - 4140. Retrieved 2010/09/04.
• 2、 Debart, Francoise,Vasseur, Jean-Jacques,Sanghvi, Yogesh S.,Cook, P. Dan. "Intermolecular Radical C-C Bond Formation: Synthesis of a Novel Dinucleoside Linker for Non-anionic Antisense Oligonucleosides". . p. 2645 - 2648. Retrieved 2007/10/02.