164267-52-1

Basic information

• Product Name: 5'-O-tert-butyldimethylsilyl-3'-O-(4,4'-dimethoxytriphenylmethyl)thymidine
• Synonyms: 5'-O-tert-butyldimethylsilyl-3'-O-(4,4'-dimethoxytriphenylmethyl)thymidine
• CAS NO: 164267-52-1
• Molecular Weight: 658.867
• Mol File: 164267-52-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 5'-O-tert-butyldimethylsilyl-3'-O-(4,4'-dimethoxytriphenylmethyl)thymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-tert-butyldimethylsilyl-3'-O-(4,4'-dimethoxytriphenylmethyl)thymidine(164267-52-1)
• EPA Substance Registry System: 5'-O-tert-butyldimethylsilyl-3'-O-(4,4'-dimethoxytriphenylmethyl)thymidine(164267-52-1)

Safety Data

• Hazardous Substances Data: 164267-52-1(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 50-89-5 thymidine 
• 76054-81-4 3'-O-(4,4'-dimethoxytrityl)thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 40733-28-6 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine 

Downstream Products

• 1146622-45-8 C₅₆H₆₉N₆O₁₅P 
• 1146622-43-6 C₄₇H₅₂N₄O₁₄ 
• 1146622-41-4 C₅₃H₆₆N₄O₁₄Si 
• 215318-35-7 3'-O-(p,p'-dimethoxytrityl)thymidine 5'-(allyl N,N-diisopropylphosphoramidite) 
• 235744-87-3 5'-O-(tert-butyldimethylsilyl)-3'-O-(tetrahydropyranyl)-(N₃-benzoyl)thymidine 
• 235744-89-5 5'-O-(tert-butyldimethylsilyl)-(N₃-benzoyl)thymidine 
• 903570-49-0 3-(2-Benzenesulfonyl-ethyl)-1-{(2R,4S,5R)-5-(3,4-bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 903570-39-8 1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione 
• 903570-48-9 3-(2-Benzenesulfonyl-ethyl)-1-[(2R,4S,5R)-5-(3,4-bis-benzyloxy-benzyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 903570-47-8 1-{(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione 
• 903570-37-6 1-[4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione 
• 76054-81-4 3'-O-(4,4'-dimethoxytrityl)thymidine 
• 179178-49-5 N-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,2,2-trifluoro-acetamide 
• 179178-43-9 5'-O-(4,4'-dimethoxytrityl)-4'-C-methoxymethylenethymidine 

Relevant articles and documents

4′-Epi-DNA: A DNA Mimic Containing 4′-hydroxymethyl-α-l-Xylo-Thymidine with Compact Backbone like RNA

Synthesis of C4′-epi-DNA containing 3′→ 5″ linkages is reported for the first time. Crystal structure study of the monomer indicated that though the dihedral angle O3′-C3′-C4′-C5″ in this case would be like in RNA, the sugar conformation would remain like that in DNA. The study of the effect of this backbone configuration in DNA with respect to its binding to cDNA and RNA is reported in this note.

A new reagent system for efficient silylation of alcohols: Silyl chloride-N-methylimidazole-iodine

It was found that reactions of alcohols with silyl chlorides in the presence of N-methylimidazole were significantly accelerated by the added iodine, and on this basis a general, and high yielding method for efficient silylation of primary, secondary, and

2-(Phenylthio)ethyl as a novel two-stage base protecting group for thymidine analogues

2-(Phenylthio)ethyl is here proposed for temporary masking the thymine residue in the synthesis of sugar modified thymidine derivatives. This protection has been devised as a 'two-stage' system. The 2-(phenylthio)ethyl residue can be easily and regiospecifically inserted at the N3-position of the pyrimidine by a Mitsunobu reaction with 2-(phenylthio)ethanol and is perfectly stable also to strongly basic conditions. This allowed us to selectively achieve O-alkylation of the ribose moieties in satisfactory yields, avoiding undesired base alkylations. After oxidation of the thioether to sulfone, the thymine protecting group can be totally removed, by a β-elimination mechanism, upon the same basic treatment required for the final deprotection and detachment of oligonucleotides from the support in solid-phase synthesis protocols. Georg Thieme Verlag Stuttgart.