104218-44-2

Basic information

• Product Name: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE
• Synonyms: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE;1-(3-mesyloxy-5-trityloxymethyl-2-D-threofuryl)thymine
• CAS NO: 104218-44-2
• Molecular Formula: C₃₀H₃₀N₂O₇S
• Molecular Weight: 562.64
• EINECS: 406-360-9
• Mol File: 104218-44-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE(104218-44-2)
• EPA Substance Registry System: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE(104218-44-2)

Safety Data

• Statements: 53
• Safety Statements: 61
• Hazardous Substances Data: 104218-44-2(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 52486-19-8 1-(β-D-xylofuranosyl)-thymine 
• 16053-52-4 threothymidine 
• 7791-71-1 5'-O-tritylthymidine 
• 50-89-5 thymidine 
• 141690-73-5 3'-Tosyl-5'-O-trityl thymidine 
• 124-63-0 methanesulfonyl chloride 
• 55612-11-8 5'-O-trityldeoxyxylothymidine 

Downstream Products

• 1446526-83-5 3'-deoxy-3'-N-[(ethoxycarbonyl)methylamino]-5'-O-tritylthymidine 
• 1446526-87-9 3′-deoxy-3′-S-[(methoxycarbonyl)methylsulfonyl]-5′-O-tritylthymidine 
• 1446526-84-6 3′-deoxy-3′-S-[(carboxymethyl)thio]-5′-O-tritylthymidine 
• 1085503-18-9 C₃₁H₃₂N₂O₄S 
• 1085503-20-3 C₃₆H₃₄N₂O₄S 
• 1085503-19-0 C₃₂H₃₄N₂O₄S 
• 127682-54-6 3'-deoxy-3'-methylthio-5'-O-tritylthymidine 
• 65475-49-2 1-(5-O-trityl-β-D-glycero-pentofuran-3-ulosyl)thymine 
• 118466-41-4 (E)-(R)-1-Butylamino-4-hydroxy-5-trityloxy-pent-1-en-3-one 
• 118466-40-3 Acetic acid 2-trityloxymethyl-furan-3-yl ester 
• 65475-52-7 4,5-dihydro-5-trityloxymethylfuran-4-one 
• 25526-93-6 alovudine 
• 153907-32-5 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-31-4 3'-benzylamino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 

Relevant articles and documents

Solid-phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences

Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3′→5′ direction and involves coupling of 3′-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5′-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated.

Process for the deoxygenation of nucleosides

An efficient process for the deoxygenation of 2'- and or 3'-hydroxyl groups of a nucleoside that includes reacting the hydroxyl group with 3-halopropionitrile or 2-nitroethylhalide and carbon disulfide in base to form a 2'- or 3'-(cyanoethylthio or nitroethylthio)thiocarbonyl, that is reductively eliminated and replaced with hydrogen. The deoxygenation process can be used in a wide variety of nucleoside syntheses that require the elimination of the 2'- or 3'-hydroxyl groups, including the preparation of 3'-substituted-2',3'-dideoxynucleosides such as 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine.

Chemical process

This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving: i) Conversion of D-xylose to a 1-(β-D-xylofuranosyl)thymine derivative; ii) 2?-Deoxygenation of the thymine derivative; and iii) 3?-Azidation of the 2?-deoxy compound.