219854-34-9

Usage

Uses

Used in Pharmaceutical Industry:
3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose is used as a reactant for the preparation of abasic locked nucleic acid derivatives. These derivatives are essential for stability analysis in the development of novel therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose is used as a key intermediate in the synthesis of oligonucleotides containing novel thymidine moieties. These oligonucleotides have potential applications in various areas, including drug development and molecular biology research.
Overall, 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose is a versatile compound with applications in both the pharmaceutical and chemical synthesis industries. Its unique structure and reactivity make it a valuable tool for the development of new drugs and the synthesis of complex organic molecules.

Upstream product

• 100-39-0 benzyl bromide 
• 124-63-0 methanesulfonyl chloride 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 153186-10-8 ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol 

Downstream Products

• 221229-65-8 1,2-di-O-acetyl-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-L-lyxofuranose 
• 296250-84-5 (2S,3S,4S)-4-(4,4'-dimethoxytrityl)oxymethyl-3-hydroxy-2-((thymin-1-yl)methyl)tetrahydrofuran 
• 223591-10-4 (2R,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-formyl-4-hydroxytetrahydrofuran 
• 223590-98-5 (1S,3RS,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-methoxy-2,5-dioxabicyclo[2.2.1]heptane 
• 223591-08-0 (1S,4S,7S)-7-benzyloxy-1-benzyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane 
• 223590-99-6 (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran 
• 223591-04-6 (1R,4S,7S)-1-(4,4'-dimethoxytrityl)oxymethyl-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane 
• 223591-06-8 (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran 
• 296250-78-7 (2S,3S,4S)-3,4-dihydroxy-4-hydroxymethyl-2-((p-toluenesulfonyloxy)methyl)tetrahydrofuran 
• 296250-81-2 (2S,3S,4S)-3-hydroxy-4-hydroxymethyl-3-O,O-(hydroxymethyl)-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-((p-toluenesulfonyloxy)methyl)tetrahydrofuran 
• 296250-69-6 (2S,3S,4S)-4-acetoxy-3-benzyloxy-4-benzyloxymethyl-2-((p-toluenesulfonyl)oxymethyl)tetrahydrofuran 
• 296250-70-9 (2S,3S,4S)-4-acetoxy-3-benzyloxy-4-benzyloxymethyl-2-(thymin-1-ylmethyl)tetrahydrofuran 
• 296250-79-8 (2S,3S,4R)-3,4-dihydroxy-4-hydroxymethyl-3-O,O-(hydroxymethyl)-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-((p-toluenesulfonyloxy)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

CYCLIC DINUCLEOTIDES AS STING AGONISTS

Disclosed are compounds, compositions and methods for treating of diseases, syndromes, or disorders that are affected by the modulation of STING. Such compounds are represented by Formula (I) as follows: wherein B2,X2, R2a, R2b, R2c, Z-M-Y, Y1-M1Z1, B1, X1, R1a, R1b, R1c are as defined herein.

CROSSLINKED NUCLEIC ACID GUNA, METHOD FOR PRODUCING SAME, AND INTERMEDIATE COMPOUND

The present invention provides a method for producing guanidine crosslinked artificial nucleic acid (abbreviated hereinafter as GuNA), and an intermediate compound for the production thereof. Specifically, the present invention provides a method for producing a compound represented by general formula I: (in the formula, R1, R2, R3, R4, R5, R6, m and ring A are as defined in the specification) or a salt thereof wherein a reducing agent is reacted with a compound represented by general formula II: (in the formula, R1, R2, R3, R4, R5, R6, m, and ring A′ are as defined in the specification).

Steric effects in the tuning of the diastereoselectivity of the intramolecular free-radical cyclization to an olefin as exemplified through the synthesis of a carba-pentofuranose scaffold

Two free-radical cyclization reactions with the radical at the chiral C4 of the pentose sugar and the intramolecularly C1-tethered olefin (on radical precursors 8 and 17) gave a new diastereospecific C4-C8 bond in dimethylbicyclo[2.2.1]heptane 9, whereas the new C4-C7 bond in 7-methyl-2-oxabicyclo[2.2.1]heptanes 18a/18b gave trans and cis diastereomers, in which the chirality of the C4 center is fully retained as that of the starting material. It has been shown how the chemical nature of the fused carba-pentofuranose scaffolds, dimethylbicyclo[2.2.1]heptane 9 vis-a-vis 7-methyl-2-oxabicyclo[2.2.1]heptanes 18a/18b (C7-Me in the former versus 2-O- in the latter), dictates the stereochemical outcome both at the Grignard reaction step as well as in the free-radical ring-closure reaction. The formation of pure 1,8-trans-bicyclo[2.2.1]heptane 9 from 8 suggests that the boat-like transition state is favored due to the absence of steric clash of the bulky 1(S)-O-p-methoxybenzyl (PMB) and 7(R)-Me substituents (both in the α-face) with that of the 8(R)-CH2? radical in the β-face. The conversion of 17 → 18a-7(S) and 18b-7(R) in 6:4 ratio shows that the participation of both the chair- and the boat-like transition states is likely.

Oligonucleotides containing novel 4'-C- or 3'-C-(aminoalkyl)-branched thymidines

The synthesis of four novel 3'-C-branched and 4'-C-branched nucleosides and their transformation into the corresponding 3'-O-phosphoramidite building blocks for automated oligonucleotide synthesis is reported. The 4'-C-branched key intermediate 11 was synthesized by a convergent strategy and converted to its 2-O-methyl and 2'-deoxy-2'-fluoro derivatives, leading to the preparation of novel oligonucleotide analogues containing 4'-C-(aminomethyl)-2'-O-methyl monomer X and 4'-C-(aminomethyl)-2'-deoxy-2'-fluoro monomer Y (Schemes 2 and 3). In general, increased binding affinity towards complementary single- stranded DNA and RNA was obtained with these analogues compared to the unmodified references (Table 1). The presence of monomer X or monomer Y in a 2'-O-methyl-RNA oligonucleotide had a negative effect on the binding affinity of the 2'-O-methyl-RNA oligonucleotide towards DNA and RNA. Starting from the 3'-C-allyl derivative 28, 3'-C-(3-aminopropyl)-protected nucleosides and 3'- O-phosphoramidite derivatives were synthesized, leading to novel oligonucleotide analogues containing 3'-C-(3-aminopropyl)thymidine monomer Z or the corresponding 3'-C-(3-aminopropyl)-2'-O,5-dimethyluridine monomer W (Schemes 4 and 5). Incorporation of the 2'-deoxy monomer Z induced no significant changes in the binding affinity towards DNA but decreased binding affinity towards RNA, while the 2'-O-methyl monomer Z induced decreased binding affinity towards DNA as well as RNA complements (Table 2).

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.

A new synthetic approach towards α- and β-LNA (locked nucleic acids)

A bicyclo[2.2.1] phenyl thioglycoside was efficiently synthesised and introduced as the key synthon in a novel method for convergent synthesis of β-LNA-nucleosides as well as their α-configurated isomers. An acid-induced ring-opening reaction on the corre

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