1027758-99-1

Upstream product

• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 72261-44-0 1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 1418031-58-9 C₂₂H₃₄O₆Si 
• 1418031-57-8 C₂₅H₄₀O₆Si 

Relevant academic research and scientific papers

Total synthesis of 6- o -benzoylzeylenol from diacetone glucose

A total synthesis of 6-O-benzoylzeylenol from diacetone glucose is described. The key steps were a crossed aldol-Cannizzaro reaction to create a quaternary carbon stereocenter, and cyclization through ring closure metathesis (RCM). Of the four stereogenic centers, two were derived from diacetone glucose, the quaternary stereocenter was created by means of the crossed aldol-Cannizzaro reaction, and the fourth stereogenic center was produced by a Sharpless asymmetric epoxidation. Finally, cyclization through RCM and deprotection by removal of a benzyl group with titanium(IV) chloride gave the target molecule. Georg Thieme Verlag Stuttgart New York.

TRICYCLIC NUCLEIC ACID ANALOGS

The present disclosure provides tricyclic nucleosides and oligomeric compounds prepared therefrom. The tricyclic nucleosides each have a tricyclic ribosyl sugar moiety wherein a bridge between the 2' and 4' ribosyl ring carbon atoms further comprises a fused carbocyclic or heterocyclic ring. The tricyclic nucleosides are expected to be useful for enhancing properties of oligomeric compounds including for example binding affinity and nuclease resistance.

Introduction of vinyl and hydroxymethyl functionalities at C-4 of glucose-derived substrates: Synthesis of spirocyclic, bicyclic, and tricyclic nucleosides

(Chemical Equation Presented) Installing hydroxymethyl and hydroxyethyl substitutions at C-4 through vinylation and hydroboration-oxidation reactions of the C-4 bis-hydroxymethyl derivative of D-glucose based substrate, and inserting heteroatoms thereafter permitted formation of N-, O-, or S-heterocycles leading to [4,5]-or [5,5]-spirocycles and a bicyclo[3.3.0]octane product. Some of the spirocycles were converted to spironucleosides under Vorbrueggen glycosidation reaction conditions. Similarly, the bicyclic product was elaborated to the corresponding bicyclic nucleoside as well as an unexpected tricyclic nucleoside.