206055-67-6

Basic information

• Product Name: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
• Synonyms: 1-(2'-O,4-C-Methylene-beta-D-ribofuranosyl)thymine;1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione;1-(2'-O-4-C-Methylene-b-D-ribofuranosyl)thymine;LNA-002 1-(2'-O, 4-C-Methylene-β-D- ribofuranosyl)thyMine;5-Methyl-2'-O,4'-C-methyleneuridine
• CAS NO: 206055-67-6
• Molecular Formula: C₁₁H₁₄N₂O₆
• Molecular Weight: 270.24
• Mol File: 206055-67-6.mol

Chemical Properties

• Melting Point: 196-198 °C
• Appearance: /
• Density: 1.598
• PKA: 9.46±0.10(Predicted)
• CAS DataBase Reference: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione(206055-67-6)
• EPA Substance Registry System: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione(206055-67-6)

Safety Data

• Hazardous Substances Data: 206055-67-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione is used as a compound of interest for its potential biological activity. Its unique structure may contribute to the development of new pharmaceutical agents, particularly in the context of drug discovery and design.
Used as a Starting Material for Synthesis:
In the field of organic chemistry, 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione serves as a valuable starting material for the synthesis of other complex organic compounds. Its functional groups and structural features can be further modified to create novel molecules with specific therapeutic properties or applications.

Upstream product

• 212970-84-8 (1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 65-71-4 thymin 
• 219854-35-0 methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside 
• 206055-62-1 (1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 290348-24-2 (3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2595-05-3 Diacetone D-glucose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 67-56-1 methanol 
• 209968-87-6 1-(2-O-acetyl-3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine 
• 209968-88-7 1-(3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine 

Downstream Products

• 902452-83-9 Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dioxa-bicyclo[2.2.1]hept-7-yl ester 
• 1430073-63-4 5'-O-p-toluenesulfonyl-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidine 
• 1430073-62-3 5'-O-p-toluenesulfonyl-2'-O,4'-C-methylenethymidine 
• 1430073-72-5 1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-2-O,4-C-methylenethymidin-5-yl)mercaptoacetamide 
• 1430073-69-0 1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-3-O-tert-butyldiphenylsilyl-2-O,4-C-methylene-thymidin-5-yl)mercaptoacetamide 
• 1430073-65-6 2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid 
• 1430073-64-5 ethyl 2-S-(3'-O-tert-butyldiphenylsilyl-5'-deoxy-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetate 
• 1257646-78-8 (1R,3R,4R,7S)-1-benzoyloxymethyl-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 936616-57-8 C₂₁H₂₅ClN₃O₁₀P 
• 936616-56-7 C₂₇H₃₀N₃O₁₀P 
• 936616-55-6 C₂₁H₂₆N₃O₁₀P 
• 206055-81-4 (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 

Relevant articles and documents

Why carba-LNA-modified oligonucleotides show considerably improved 3′-exonuclease stability compared to that of the LNA modified or the native counterparts: A michaelis-menten kinetic analysis

(Figure Presented) In this study, 12 different native or LNA, carba-LNA-modified dinucleoside phosphates were designed as simple chemical models to study how carba-LNA modifications improve the 3′-exonuclease (SVPDE in this study) resistance of internucleotidic phosphate compared to those exhibited by LNA-modified and the native counterparts. Michaelis-Menten kinetic studies for dimers 3 - 7, in which the LNA or carba-LNA modifications are located at the 5′-end, showed that (i) increased 3′-exonuclease resistance Of 5′[LNA-T]pT (3) compared to the native 5′Tp (1) was mainly attributed to steric hindrance imposed by the LNA modification that retards the nuclease binding (K M) and (ii) digestion of 5[carba-LNA-dT]pT (4) and 5′[LNA-T]p (3), however, exhibit similar K Ms, whereas the former shows a 100 x decrease in Kcat and is hence more stable than the latter. By studying the correlation between log kcat and pKa of the departing 3′(or 6′)-OHs for 3-7, we found the pKa of 3′-OH of carbaLNA-T was 1.4 pKa units higher than that of LNA-T, and this relatively less acidic character of the 3′-OH in the former leads to the 100x decrease in the catalytic efficiency for the digestion of 5′[carbaLNA-T] pT (4). In contrast, Michaelis-Menten kinetic studies for dimers 9-12, with the LNA or carbaLNA modifications at the 3′-end, showed that the digestion of 5′Tp[LNA-T] (9) exhibited similar KM but fccat decreased around 40 times compared to that of the native 5′ TpT (1). Similar kcat values have been observed for digestion of 5′ Tp[ carba-LNA-T] (10) and 5′TP[LNA-T] (9). The higher stability of carbaLNA modified dimer 10 compared with LNA modified dimer 9 comes solely from the increased KM.

α-LNA, locked nucleic acid with α-D-configuration

The bicyclic thymine monomer of α-LNA (αT(L)) was efficiently synthesised and used in the synthesis of α-LNA sequences: incorporation of single αT(L)-monomers in α-configured oligothymidylates destabilises the affinity towards both complementary DNA and R

NOVEL PROCESS FOR MAKING ALLOFURANOSE FROM GLUCOFURANOSE

The present invention relates to the manufacture of allofuranose from glucofuranose as defined in the description and in the claim. Allofuranos is an intermediate in the manufacture of oligonucleotides which can be used as a medicament.

Chemoenzymatic convergent synthesis of 2'-o,4'-c-methyleneribonucleosides

Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully

IMPROVED SYNTHESIS OF ?2.2.1|BICYCLO NUCLEOSIDES

A synthesis of [2.2.1]bicyclo nucleosides which is shorter and provides higher overall yields proceeds via the key intermediate of the general formula III, wherein R4 and R5 are, for instance, sulfonates and R7 is, for instance, a halogen or an acetate. F

Bicyclonucleoside and oligonucleotide analogue

An oligo- or polynucleotide analogue having one or more structures of the general formula where B is a pyrimidine or purine nucleic acid base, or an analogue thereof, is disclosed. The use of this analogue provides an oligonucleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.

Novel bicyclonucleoside and oligonucleotide analogue

An oligo- or polynucleotide analogue having one or more structures of the general formula where B is a pyrimidine or purine nucleic acid base, or an analogue thereof, is disclosed. The use of this analogue provides an oligonucleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.

Synthesis of [2.2.1]bicyclo nucleosides

A synthesis of [2.2.1]bicyclo nucleosides which is shorter and provides higher overall yields proceeds via the key intermediate of the general formula III, wherein R4 and R5 are, for instance, sulfonates and R7 is, for ins

α-LNA (locked nucleic acid with α-D-configuration): Synthesis and selective parallel recognition of RNA

α-LNA is presented as a stereoisomer of LNA (locked nucleic acid) with α-D-configuration. Three different approaches towards the thymine α-LNA monomer as well as the 5-methylcytosine α-LNA monomer are presented. Different α-LNA sequences have been synthesised and their hybridisation with complementary DNA and RNA has been evaluated by means of thermal stability experiments and circular dichroism spectroscopy. In a mixed pyrimidine sequence, α-LNA displays unprecedented parallel-stranded and selective RNA binding. Furthermore, a remarkable selectivity for hybridisation with RNA over DNA is indicated.

Synthesis and evaluation of α-LNA

Three different synthetic routes to the α-configured LNA thymine monomer starting from D-allose or D-arabinose were investigated. The introduction of one or four α-LNA monomers into α-DNA had a destabilizing effect on the duplexes. However, a fully modifi