99152-41-7

Basic information

• Product Name: 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)uracil
• Synonyms: 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)uracil
• CAS NO: 99152-41-7
• Molecular Weight: 452.42
• Mol File: 99152-41-7.mol

Chemical Properties

• CAS DataBase Reference: 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)uracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)uracil(99152-41-7)
• EPA Substance Registry System: 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)uracil(99152-41-7)

Safety Data

• Hazardous Substances Data: 99152-41-7(Hazardous Substances Data)

Upstream product

• 118243-92-8 1,2-sulfite de 3,5-di-O-benzoyl-α-D-xylofuranose 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 66-22-8 uracil 
• 191538-37-1 3,5-di-O-benzoyl-α-D-xylo-furanose 1,2-thiocarbonate 
• 685137-15-9 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzoyl-β-D-xylo-furanosyl)uracil 
• 99355-31-4 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-xylofuranosyl)uracil 

Downstream Products

• 883239-83-6 1-(3',5'-di-O-benzoyl-2'-O-mesyl-β-D-xylo-furanosyl)uracil 
• 117257-94-0 1-(2-O-phenoxythiocarbonyl-3,5-di-O-benzoyl-β-D-xylofuranosyl)uracil 
• 117257-95-1 C₄₇H₃₈N₄O₁₆S 

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.

SYNTHESE DE NUCLEOSIDES PYRIMIDIQUES NON PROTEGES EN O-2'A PARTIR DE SULFITES CYCLIQUES EN C-1-C-2

Treatment of 3,5,6-tri-O-benzoyl-α-D-glucofuranose 1,2-sulfite with an excess of bis(trimethylsilyl) uracil, in fusion processes without any catalyst, afforded an excellent yield of 1-(3,5,6-tri-O-benzoyl-2-O-trimethylsilyl-β-D-glucopyranosyl)uracil, which was readily hydrolyzed in slightly acid conditions to give in almost quantitative yield 1-(3,5,6-tri-O-benzoyl-β-D-glucofuranosyl)uracil.This new synthetic method for nucleosides unprotected at O-2' was also tested in other sugar series.In some cases, only the 1',2'-trans-nucleosides were obtained, but in others, small yields (3-10percent) of 1',2'-cis-nucleosides were detected.The α-to-β ratio seems to be dependent on the reaction temperature. 2,4-Dimethoxypyrimidine also reacted with sugar 1,2-sulfites and 4-O-methyl-1-(3,5,6-tri-O-benzyl-β-D-glucopyranosyl)-2-pyrimidinone was prepared in 85percent yield from 3,5,6-tri-O-benzyl-α-D-glucopyranose 1,2-sulfite.

Nucleic acid related compounds. 53. Synthesis and biological evaluation of 2'-deoxy-&β-threo-pentofuranosyl nucleosides. "Reversion to starting alcohol" in Barton-type reductions of thionocarbonates

Treatment of selectively 3',5'-protected β-D-xylofuranosyl nucleosides (4) with phenyl chlorothionocarbonate and DMAP followed by hydrogenolysis of the resulting (2'-O-phenoxythiocarbonyl) phenyl thionocarbonate esters (6) with tributylstannane/AIBN, and