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
• Article Data: 19

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

General Description

The chemical "1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione" is an organic compound with a complex molecular structure. It is a derivative of alpha-L-lyxofuranosyl and pyrimidinedione, containing a hydroxymethyl group and a methyl group. 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione has potential applications in the field of pharmaceuticals and may be of interest for its biological activity or as a starting material for the synthesis of other compounds. Its precise chemical properties and potential uses would require further investigation and study.

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 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 
• 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 
• 209968-86-5 4-C-[(phenylmethoxy)methyl]-3-O-(phenylmethyl)-1,2-diacetate 5-(4-methylbenzenesulfonate)-L-lyxofuranose 
• 153186-13-1 3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-1,2-O-isopropylidene-α-D-ribofuranose 
• 206055-48-3 4-C-acetoxymethyl-1,2-di-O-acetyl-3,5-di-O-benzyl-D-ribofuranose 
• 206055-49-4 [(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate 
• 206055-57-4 1-[(2R,3R,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-3-hydroxy-5-(hydroxymethyl)tetra-hydrofuran-2-yl]-5-methylpyrimidine-2,4-dione 
• 206055-83-6 4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 219854-34-9 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose 

Downstream Products

• 206055-75-6 (1R,3R,4R,7S)-3-(thymine-1-yl)-1-(4,4′-dimethoxytrityloxy)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane 
• 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 
• 936616-56-7 C₂₇H₃₀N₃O₁₀P 
• 936616-57-8 C₂₁H₂₅ClN₃O₁₀P 
• 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 

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.

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.

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