3',5'-Di-O-mesylthymidine

Base Information

• Chemical Name: 3',5'-Di-O-mesylthymidine
• CAS No.: 56822-33-4
• Molecular Formula: C12H18N2O9S2
• Molecular Weight: 398.415
• Mol file: 56822-33-4.mol

Synonyms:3',5'-Bis-O-(methylsulfonyl)thymidine;

Chemical Property of 3',5'-Di-O-mesylthymidine

Chemical Property:

• Refractive Index: 1.585
• PSA: 167.59000
• Density: 1.59 g/cm³
• LogP: 0.61510

Purity/Quality:

99% ^*data from raw suppliers

3',5'-DI-ORTHO-MESYLTHYMIDINE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3',5'-Di-O-mesylthymidine

There total 5 articles about 3',5'-Di-O-mesylthymidine 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: 91.0%

methanesulfonyl chloride (124-63-0) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 3',5'-di-O-mesylthymidine (56822-33-4)

Guidance literature:

With triethylamine; In pyridine; at 0 - 20 ℃;

DOI:10.1021/jacs.9b09937

Reference yield: 52.0%

methanesulfonic acid (75-75-2,98527-29-8) + 1-(2,3'-Anhydro-5'-O-methylsulfonyl-2-deoxy-β-D-threo-pentofuranosyl)thymine (15981-86-9) → 3',5'-di-O-mesylthymidine (56822-33-4)

Guidance literature:

In 1,4-dioxane; for 1.5h; Heating;

DOI:10.1021/jm00109a017

Reference yield: 29.5%

1-(2,3'-Anhydro-5'-O-methylsulfonyl-2-deoxy-β-D-threo-pentofuranosyl)thymine (15981-86-9) → 3',5'-di-O-mesylthymidine (56822-33-4) + 2,5'-Anhydro-3'-O-mesylthymidin + 3'-deoxy-3'-fluoro-5'-O-mesylthymidine (51247-06-4)

Guidance literature:

In N,N-dimethyl-formamide; at 110 ℃; for 1.25h;

upstream raw materials:

methanesulfonyl chloride

thymidine

methanesulfonic acid

1-(2,3'-Anhydro-5'-O-methylsulfonyl-2-deoxy-β-D-threo-pentofuranosyl)thymine

Downstream raw materials:

1-(2,3'-Anhydro-5'-O-methylsulfonyl-2-deoxy-β-D-threo-pentofuranosyl)thymine

3'-O-mesylthymidine

C₁₇H₁₅N₃O₈

stavudin

Refernces

• 1、 Barral, Karine,Priet, Stéphane,De Michelis, Céline,Sire, Joséphine,Neyts, Johan,Balzarini, Jan,Canard, Bruno,Alvarez, Karine. "Synthesis and antiviral activity of boranophosphonate isosteres of AZT and d4T monophosphates". . p. 849 - 856. Retrieved 2010.
• 2、 Skakuj, Kacper,Bujold, Katherine E.,Mirkin, Chad A.. "Mercury-Free Automated Synthesis of Guanidinium Backbone Oligonucleotides". supporting information. p. 20171 - 20176. Retrieved 2020/01/02.