446862-76-6

Basic information

• Product Name: 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose
• Synonyms: 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose
• CAS NO: 446862-76-6
• Molecular Weight: 698.863
• Mol File: 446862-76-6.mol

Chemical Properties

• CAS DataBase Reference: 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose(446862-76-6)
• EPA Substance Registry System: 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose(446862-76-6)

Safety Data

• Hazardous Substances Data: 446862-76-6(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 212970-72-4 {3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 108-24-7 acetic anhydride 
• 212970-73-5 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyl)oxymethyl-α-D-erythro-pentofuranose 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 

Downstream Products

• 260269-35-0 N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine 
• 446862-78-8 N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine 
• 260269-33-8 5'-O-tert-butyldiphenylsilyl-5-methyl-4'-C-(p-toluenesulfonyl)oxymethyluridine 
• 260269-39-4 N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methyleneadenosine 
• 260269-38-3 N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine 
• 260269-37-2 5'-O-tert-butyldiphenylsilyl-5-methyl-3'-O,4'-C-methyleneuridine 
• 260269-36-1 5'-O-tert-butyldiphenylsilyl-N²-isobutyryl-4'-C-(p-toluenesulfonyl)oxymethylguanosine 
• 260269-29-2 5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-5-methyl-4'-C-(p-toluenesulfonyl)oxymethyluridine 
• 260269-31-6 N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine 
• 446862-77-7 N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine 

Relevant articles and documents

Synthesis and conformation of 3′,4′-BNA monomers, 3′-O,4′-C-methyleneribonucleosides

In order to develop novel 2′,5′-linked oligonucleotide analogues aimed for antivirus reagents and antisense/antigene oligonucleotides, novel nucleoside analogues, 3′-O,4′-C-methyleneribonucleosides (3′,4′-BNA monomers) were synthesized via two synthetic routes. The first route starting from uridine utilized a regioselective ring-closure reaction of the 4′-C-(p-toluenesulfonyl)oxymethyluridine derivative. The second route involved a coupling reaction of 1,2,3-tri-O-acetyl-4-C-(p-toluenesulfonyl)oxymethylribofuranose derivative with nucleobases followed by oxetan-ring formation to afford the 3′,4′-BNA monomers bearing all four nucleobases. By means of 1H NMR, X-ray crystallography and computational analysis, the sugar puckering of the 3′,4′-BNA monomers was found to be restricted in S-conformation (C1′-exo-C2′-endo puckering mode).