5'-O-Trityl-3'-O-mesylthymidine

Base Information

• Chemical Name: 5'-O-Trityl-3'-O-mesylthymidine
• CAS No.: 104218-44-2
• Molecular Formula: C30H30 N2 O7 S
• Molecular Weight: 562.643
• European Community (EC) Number: 406-360-9
• NSC Number: 142847,254065
• Mol file: 104218-44-2.mol

Synonyms:42214-24-4;5'-O-TRITYL-3'-O-MESYLTHYMIDINE;104218-44-2;NSC254065;NLAIOTWSOVURMN-UHFFFAOYSA-N;NSC142847;NSC-142847;NSC-254065

Chemical Property of 5'-O-Trityl-3'-O-mesylthymidine

Chemical Property:

• PSA: 125.07000
• LogP: 4.56680
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 562.17737247
• Heavy Atom Count: 40
• Complexity: 991

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Statements: 53
• Safety Statements: 61

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)OS(=O)(=O)C

Technology Process of 5'-O-Trityl-3'-O-mesylthymidine

There total 7 articles about 5'-O-Trityl-3'-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: 92.0%

methanesulfonyl chloride (124-63-0) + 5'-O-trityldeoxyxylothymidine (55612-11-8) → 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine (104218-44-2)

Guidance literature:

With pyridine; for 10h; Heating;

DOI:10.1016/0040-4039(88)85124-4

Reference yield:

trityl chloride (76-83-5) + 1-(β-D-xylofuranosyl)-thymine (52486-19-8,642082-80-2) → 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine (104218-44-2)

Guidance literature:

With triethylamine; In pyridine;

Reference yield:

trityl chloride (76-83-5) + threothymidine (16053-52-4,28854-96-8,3545-96-8,50-88-4) → 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine (104218-44-2)

Guidance literature:

In pyridine;

upstream raw materials:

methanesulfonyl chloride

5'-O-trityldeoxyxylothymidine

trityl chloride

5'-O-tritylthymidine

Downstream raw materials:

1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine

5-Methyl-1-((2R,4S,5S)-4-propylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

1-((2R,4S,5S)-4-Allylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

3'-deoxy-3'-N-[(ethoxycarbonyl)methylamino]-5'-O-tritylthymidine

Refernces

• 1、 Belostotskii,Lexner,Hassner. "New nucleoside heteroanalogues: Desoxynucleoside selenocyanates". . p. 1181 - 1184. Retrieved 2007/10/03.
• 2、 Wilson, I. K.,Chatterjee, S.,Wolf, W.. "Synthesis of 3'-fluoro-3'-deoxythymidine and studies of its 18F-radiolabeling, as a tracer for the noninvasive monitoring of the biodistribution of drugs against AIDS". . p. 283 - 289. Retrieved 2007/10/02.