223591-10-4

Upstream product

• 219854-37-2 methyl 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranoside 
• 223590-98-5 (1S,3RS,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-methoxy-2,5-dioxabicyclo[2.2.1]heptane 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 219854-34-9 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose 
• 219854-35-0 methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside 
• 153186-10-8 ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol 
• 459804-74-1 methyl 2-O,4-C-methylene-β-D-ribofuranoside 
• 260434-52-4 methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside 
• 260434-51-3 methyl 2,3-O-benzylidene-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside 
• 212970-66-6 methyl 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-(p-toluenesulfonyloxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside 
• 212970-67-7 methyl 5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside 
• 212970-65-5 methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside 
• 260434-54-6 methyl 3-O-benzyl-2-O,4-C-methylene-β-D-ribofuranoside 

Downstream Products

• 260439-74-5 5-(3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl)-2-(methylthio)oxazole 
• 260439-84-7 5-(3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl)-2-(methylthio)oxazole 
• 260434-57-9 5-(3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl)-2-phenyloxazole 
• 260434-56-8 5-(3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl)-2-phenyloxazole 
• 223590-99-6 (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran 
• 260434-59-1 2-(3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl)pyridine 
• 260434-58-0 2-(3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl)pyridine 
• 260434-61-5 3-(3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl)-1-(triisopropylsilyl)pyrrole 
• 260434-60-4 3-(3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl)-1-(triisopropylsilyl)pyrrole 
• 296250-75-4 (2S,3S,4R)-4-acetoxy-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-2-((thymin-1-yl)methyl)tetrahydrofuran 
• 296250-74-3 (2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-4-(4,4'-dimethoxytrityl)oxymethyl-4-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran 
• 296250-76-5 (2S,3S,4R)-4-acetoxy-3-hydroxy-4-(4,4'-dimethoxytrityl)oxymethyl-2-((thymin-1-yl)methyl)tetrahydrofuran 
• 296250-73-2 (2S,3S,4R)-3,4-dihydroxy-4-(4,4'-dimethoxytrityl)oxymethyl-2-((thymin-1-yl)methyl)tetrahydrofuran 
• 296250-80-1 (2S,3S,4R)-3-hydroxy-4-hydroxymethyl-4-O-methoxalyloxy-3-O,O-(hydroxymethyl)-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-((p-toluenesulfonyloxy)methyl)tetrahydrofuran 

Relevant academic research and scientific papers

Effective synthesis of C-nucleosides with 2′,4′-BNA modification

The effective synthesis of some C-nucleosides with 2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA) modification was accomplished by using the coupling reaction of a tetrahydrofurancarbaldehyde 1 with the magnesium or lithium derivatives of aromatic heterocycles followed by the Mitsunobu cyclization. Moreover, it was clearly shown by 1H NMR spectra and X-ray crystallography that the sugar conformation in the synthesized C-nucleosides, independent of the nucleobases, was fixed in N-form.

Synthesis of abasic locked nucleic acid and two seco-LNA derivatives and evaluation of their hybridization properties compared with their more flexible DNA counterparts

To investigate the structural basis of the unique hybridization properties of LNA (locked nucleic acid)1 three novel LNA derivatives with modified carbohydrate parts were synthesized and evaluated with respect to duplex stabilities. The abasic LNA monomer2 (X(L), Figure 1) with the rigid carbohydrate moiety of LNA but no nucleobase attached showed no enhanced duplex stabilities compared to its more flexible abasic DNA counterpart (X, Figure 1). These results suggest that the exceptional hybridization properties of LNA primarily originate from improved intrastrand nucleobase stacking and not backbone preorganization. Two monocyclic seco-LNA derivatives, obtained by cleavage of the C1' - O4' bond of an LNA monomer or complete removal of the O4' - furanose oxygen atom (Z(L) and dZ(L), respectively, Figure 1), were compared to their acyclic DNA counterpart3 (Z, Figure 1). Even though they are more constrained than Z, the seco-LNA derivatives Z(L) and dZ(L) destabilize duplex formation even more than the flexible seco-DNA monomer Z.

Synthesis of conformationally locked C-nucleosides having a 2,5- dioxabicyclo [2.2.1] heptane ring system

Some novel C-nucleosides having a 2,5-dioxabicyclo[2.2.1]heptane ring system were successfully synthesized via the coupling reaction of tetrahydrofurancarbaldehyde 1 with the lithium and the magnesium derivatives of aromatic heterocycles.

Investigation of restricted backbone conformations as an explanation for the exceptional thermal stabilities of duplexes involving LNA (Locked Nucleic Acid): Synthesis and evaluation of abasic LNA

In order to investigate the structural basis of the unique hybridization properties of LNA (Locked Nucleic Acid), an abasic LNA monomer (a 1-deoxy-2-O,4-C-methylene-D-ribofuranose derivative) was synthesized and evaluated with respect to influence on dupl

Synthesis and chemoselective activation of phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-1-thio-β-D-ribofuranoside: A key synthon towards α-LNA

A bicyclic thiofuranoside (phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranoside) was efficiently synthesized and introduced as the key synthon in a method for convergent synthesis of α- and β-LNA nucleosides; acid-induced ring-opening reactions of