169514-19-6

Basic information

• Product Name: N-{9-[(2S,5S)-5-(Bromomethyl-dimethyl-silanyloxy)-5,6-dihydro-2H-pyran-2-yl]-9H-purin-6-yl}-benzamide
• CAS NO: 169514-19-6
• Molecular Weight: 488.416
• Mol File: 169514-19-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-{9-[(2S,5S)-5-(Bromomethyl-dimethyl-silanyloxy)-5,6-dihydro-2H-pyran-2-yl]-9H-purin-6-yl}-benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-{9-[(2S,5S)-5-(Bromomethyl-dimethyl-silanyloxy)-5,6-dihydro-2H-pyran-2-yl]-9H-purin-6-yl}-benzamide(169514-19-6)
• EPA Substance Registry System: N-{9-[(2S,5S)-5-(Bromomethyl-dimethyl-silanyloxy)-5,6-dihydro-2H-pyran-2-yl]-9H-purin-6-yl}-benzamide(169514-19-6)

Safety Data

• Hazardous Substances Data: 169514-19-6(Hazardous Substances Data)

Upstream product

• 16532-02-8 bromomethyldimethylsilyl chloride 
• 162934-33-0 (2',3'-Dideoxy-α-D-glycero-pent-2'-enopyranosyl)-N⁶-benzoyladenine 

Relevant articles and documents

Synthesis of 3'-Deoxy-3'-C-Hydroxymethyl-aldopentopyranosyl Nucleosides and their Incorporation in Oligonucleotides. Part II.

The synthesis of 3'-deoxy-3'-C-hydroxymethyl-aldopentopyranosyl nucleosides using an intramolecular radical C-C bond formation reaction is described.This method gives good results for the synthesis of thymine and adenine nucleosides, but not for cytosine and quanine nucleosides.Dependent on the configuration (β-D-erythro or α-L-threo), the conformation of the adenine nucleosides is clearly different (axial base moiety for α-D-erythro and equatorial adenine base for α-L-threo nucleosides) which could be explained by the gauche effect.Oligonucleotides built up to 2',3'-dideoxy-3'-C-hydroxymethyl-α-L-threo-pentopyranosyl adenine are able to form duplexes with oligothymidylate although with less stability than natural dsDNA.