124572-46-9

Upstream product

• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 
• 98-88-4 benzoyl chloride 
• 124572-44-7 (5E)-3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuran-5-enose 
• 4056-10-4 1,2-O-Isopropyliden-6-O-triphenylmethyl-5-desoxy-α-D-xylo-hexofuran-5-enose 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 63-29-6 D-glucurono-6,3-lactone 
• 124572-45-8 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 7057-10-5 1,2-O-isopropylidene-α-D-5-deoxyglucurono-6,3-lactone 

Downstream Products

• 124572-55-0 N⁶-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine 
• 124572-54-9 1-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)uracil 
• 88270-97-7 1,2-di-O-acetyl-3,6-di-O-benzoyl-5-deoxy-D-ribo-hexofuranose 
• 55085-29-5 3,6-di-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 22415-88-9 9-(5-Desoxy-β-D-ribo-hexofuranosyl)adenin 
• 124572-49-2 6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-xylo-hexofuranose 
• 124572-48-1 6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 

Relevant academic research and scientific papers

Structural modifications of antisense oligonucleotides

Antisense oligonucleotides are efficient tools for the inhibition of gene expression in a sequence specific way. Natural oligonucleotides are decomposed rapidly in biological systems, which strongly restrict their application. In contrast, artificial oligonucleotides are designed to be more stable against degradation than the target mRNA, which results in a catalytic effect of the drug. Modification of the phosphate linkage has been the first successful strategy for antisense drug developments and Fomivirsene the first antisense drug in therapy. The launch of Fomivirsene has resulted in a revolutionary spin off to antisense research leading to a second generation of antisense oligonucleotides, which are stable against oligonucleotide cleaving enzymes. Among these, oligonucleotides bearing an alkoxy substituent in position 2′ were the most successful ones. The third generation of antisense oligonucleotides contains structure elements, which enhance the antisense action. Zwitterionic oligonucleotides show remarkable results, first, because the stability against ribozymes is largely increased, and secondly, because the electrostatic repulsion between the anionic sense and the zwitterionic antisense cords is minimized. Promising new target molecules in antisense reseach are oligonucleotide chimaeres, which enhance the antisense action (chimaeres with intercalators, chelators or polyamines) or enable an application as sequence specific detectors (chimaeres with biotin, fluorescein or radioligands).

USE OF 5-DEOXY-ribo-HEXOFURANOSE DERIVATIVES FOR THE PREPARATION OF 5'-NUCLEOTIDE PHOSPHONATES AND HOMORIBONUCLEOSIDES

A convenient and general method is proposed for the synthesis of 5'-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose which can easily be produced in preparative quantities from D-glucose.Phosphonate IIIa was synthesized by means of the Arbuzov reaction between 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose and triethyl phosphite.The consecutive acetolysis, condensation with uracil and N6-benzoyladenine bis-trimethylsilyl derivatives and deblocking possessed phosphonate analogs of 5'-nucleotides in good yields.The intermediate 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose derivatives were used for the preparation of homonucleosides.