201295-39-8

Upstream product

• 163070-49-3 Phenyl 3,5-di-O-isopropylidene-2-deoxy-1-thio-α-L-threo-pentofuranoside 
• 134614-93-0 Phenyl 2-deoxy-1-thio-α-L-threo-pentofuranoside 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 201287-83-4 C₂₄H₂₂N₂O₈ 
• 154463-67-9 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylo-furanosyl)thymine 
• 65-71-4 thymin 
• 201287-84-5 C₂₄H₂₂N₂O₇ 
• 163070-50-6 1-(3,5-O-Isopropylidene-2-deoxy-β-L-threo-pentofuranosyl)thymine 

Downstream Products

• 132979-41-0 1-(3-azido-2,3-dideoxy-β-L-threo-pentofuranosyl)thymine 
• 201287-85-6 1-{(2S,4S,5S)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Stereoselective Synthesis of 2'-Deoxy-β-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases

The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-α-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (α:β = 1:24 - 0:1) to afford 2'-deoxy-β-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields.The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable α form.A subsequent SN2 type attack to the intermediate will lead to the β-nucleosides.By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-β-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside.On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products.The product distribution of the regioisomers was, however, proved to change with reaction time.For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (α:β = 1:2 - 1:4.8).The isolated yields to the 9-β isomers after purification were acceptable for practical use.

New unnatural L-nucleoside enantiomers: From their stereospecific synthesis to their biological activities

Several purine and pyrimidine β-L-dideoxynucleosides were stereospecifically synthesized and their antiviral properties examined. Two of them, namely β-L-2',3'-dideoxyadenosine (β-L-ddA) and its 2',3'- didehydro derivative (β-L-d4A) were found to have significant anti-human immunodeficiency virus (HIV) and anti-hepatitis B virus (HSV) activities in cell culture.