581795-72-4

Basic information

• Product Name: C₂₇H₂₉N₃O₈S
• Synonyms: C₂₇H₂₉N₃O₈S
• CAS NO: 581795-72-4
• Molecular Weight: 555.609
• Mol File: 581795-72-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₂₇H₂₉N₃O₈S(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₇H₂₉N₃O₈S(581795-72-4)
• EPA Substance Registry System: C₂₇H₂₉N₃O₈S(581795-72-4)

Safety Data

• Hazardous Substances Data: 581795-72-4(Hazardous Substances Data)

Upstream product

• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 89000-82-8 1,2-O-thiocarbonate-3,5-di-O-benzyl-α/β-D-xylofuranose 
• 65-71-4 thymin 

Downstream Products

• 146918-94-7 1-(3',5'-di-O-benzyl-2'-O-mesyl-β-D-xylo-furanosyl)thymine 
• 134953-45-0 1-(3',5'-di-O-benzyl-β-D-xylo-furanosyl)thymine 

Relevant articles and documents

Highly β-stereoselective nucleosidation from α-D-xylo- and α-D-ribo-furanose 1,2-thiocarbonates

Cyclic 1,2-thiocarbonates of α-D-xylo- and α-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording β-nucleosides with complete stereoselectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an SN2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl) acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1′ were ascertained by chemical correlation synthesizing the corresponding 2,2′-anhydro-nucleosides.