149204-36-4

Upstream product

• 201536-71-2 1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose 
• 121687-74-9 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>thymine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 201472-26-6 (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 187843-66-9 tert-Butyl-diphenyl-((2S,5S)-5-phenylselanyl-tetrahydro-furan-2-ylmethoxy)-silane 
• 187843-63-6 tert-Butyl-diphenyl-((2S,5R)-5-phenylselanyl-tetrahydro-furan-2-ylmethoxy)-silane 

Downstream Products

• 132336-19-7 N⁴-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine 
• 132336-20-0 N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>cytosine 
• 132336-17-5 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>uracil 
• 132343-22-7 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>uracil 
• 132336-18-6 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine 
• 129778-51-4 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>thymine 
• 141684-79-9 1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>uracil 
• 125440-15-5 1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>thymine 
• 261172-26-3 (1S,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxa-bicyclo[3.1.0]hexane-6,6-dicarboxylic acid diethyl ester 
• 937723-61-0 C₂₂H₂₈O₂Si 
• 1219930-57-0 ethyl 2-((2R,3S,5S)-2-(2-acetamido-6-(diphenylcarbamoyloxy)-9H-purin-9-yl)-5-((tertbutyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl)-2-hydroxypropanoate 
• 1219930-54-7 ethyl 2-((2R,3S,5S)-2-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-5-((tertbutyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl)-2-hydroxypropanoate 
• 1219930-55-8 ethyl 2-((2R,3S,5S)-2-(6-benzamido-9H-purin-9-yl)-5-((tertbutyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl)-2-hydroxypropanoate 
• 1219930-58-1 ethyl 

Relevant academic research and scientific papers

Organocatalytic Conversion of Nucleosides to Furanoid Glycals

A class of organocatalysts that are highly active for the conversion of 2′-deoxynucleosides to furanoid glycals have been discovered. These phosphorimides, (Ph2PS)2NH and (Ph2PSe)2NH, were shown to effectively mediate persilylation of 2′-deoxynucleosides

Highly diastereoselective synthesis of modified nucleosides via an asymmetric multicomponent reaction

We have developed a practical synthesis of unique nucleoside derivatives via TiCl4 promoted multicomponent reaction of optically active dihydrofuran, ethyl pyruvate/glyoxylate, and a TMS protected nucleobase in a single-pot operation.

A concise asymmetric synthesis of (+)-muscarine from (S)-γ-hydroxymethyl-γ-butyrolactone

A highly stereoselective synthesis of (+)-muscarine iodide has been achieved in eight steps and 20% overall yield from commercially available (S)-γ-hydroxymethyl-γ-butyrolactone.

An enantioselective ring expansion route leading to furanose and pyranose nucleosides featuring spirodiketopiperazines at the anomeric position

A study directed at the enantioselective synthesis of spirodiketopiperazine homologues of hydantocidin is described. Furanoid glycals, systems that are amenable to C-5 metalation in the presence of tert- butyllithium, are readily coupled to N-protected 2,3-azetidinediones provided that at least 1 equiv of BF3·OEt2 is present to curb enolization. The resulting 1:1 mixtures of carbinols undergo smooth ring expansion to spirocyclic keto amides when heated with pyridinium p-toluenesulfonate in benzene. 1,2-Acyl shifts operate exclusively. Since attempts to engage these products in Beckmann rearrangement proved singularly unsuccessful, recourse was alternatively made to new methodology based upon sequential Baeyer- Villiger oxidation and ammonolysis. The data show that the first of these steps occurs with exclusive migration of the quaternary carbon. Furthermore, nucleophilic attack by NH3 can be directed regioselectively to the anomeric region. If heating is supplied during acid-promoted cyclization to the spirodiketopiperazines, spiropyranose derivatives are produced in a complementary process. The central issue of this synthesis effort was the utilization of 4-phenylseleno-substituted furanoid glycals so as to ultimately enable introduction of the cis-diol functionality at C-3 and C-4 (hydantocidin numbering).

Stereocontrolled Glycosylations Via Addition of Sulfur Electrophiles to Glycals

The methodology described herein examines the regio- and stereoselectivity of pyrimidine and purine glycosylations of furanoid glycals.The results show that following stereoselective sulfenylation, glycosylation of furanoid glycals, in the presence of SnC