30725-00-9

Usage

Uses

Used in Pharmaceutical Industry:
2,3-O-Isopropylidene-D-ribonic gamma-lactone is used as a key intermediate for the synthesis of C-nucleosides, which are essential in the development of antiviral and anticancer drugs. One notable example is neplanocin A, a potent antiviral agent.
Used in Biochemical Research:
2,3-O-Isopropylidene-D-ribonic gamma-lactone is used as a starting material for the preparation of GABA analogs, which are crucial in the study of the central nervous system and the development of drugs targeting neurological disorders.
Used in Organic Synthesis:
2,3-O-Isopropylidene-D-ribonic gamma-lactone is employed as a versatile building block in the synthesis of prostanoids, which are important in the study of various physiological processes and the development of drugs for conditions such as inflammation and cardiovascular diseases.

InChI:InChI=1/C8H12O5/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-6,9H,3H2,1-2H3/t4-,5-,6?/m1/s1

Upstream product

• 89538-91-0 (3aR,6R,6aR)-6-(1-Benzyloxy-1-methyl-ethoxymethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 91922-70-2 (3aR,6R,6aR)-6-(1-Benzyloxy-2-fluoro-1-methyl-ethoxymethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 67-64-1 acetone 
• 5336-08-3 D-Ribono-1,4-lactone 
• 77-76-9 2,2-dimethoxy-propane 
• 75-05-8 acetonitrile 
• 328533-43-3 2,3-O-isopropylidene-1-O-pivaloyl-α-D-ribofuranose 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 50-69-1 D-ribose 
• 18315-89-4 potassium D-ribonate 
• 532-20-7 D-Ribose 
• 75467-36-6 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 111549-93-0 5'-O-allyl-2',3'-O-isopropylidene-D-ribonic-γ-lactone 

Downstream Products

• 40519-00-4 2,3-O-Isopropylidene-5-O-(p-tolylsulfonyl)-D-ribono-1,4-lactone 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 807363-14-0 (3aR,6S,6aR)-6-(Hydroxy-methoxy-methyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 99902-66-6 4,5-dideoxy-2,3-O-isopropylidene-D-erythro-pent-4-enonic acid 
• 582312-81-0 5-O-(tert-butyldiphenylsilyl)-1'-(benzenesulfonylmethylene)-2',3'-O-isopropylidene-α-D-ribofuranose 
• 130607-26-0 [5S-(5α,7α,8β,9β)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione 
• 129744-45-2 [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione 
• 133908-91-5 [5R-(5α,7β,8α,9α)]-7-(benzyloxymethyl)-1,3-diaza-8,9-isopropylidenedioxy-6-oxaspiro[4.4]nonane-2,4-dione 
• 339540-26-0 2,5-anhydro-6-O-benzyl-1,1-dichloro-1-deoxy-3,4-O-isopropylidene-D-ribo-hex-1-enitol 
• 339540-27-1 methyl 2,5-anhydro-6-O-benzyl-2-chloro-2-deoxy-3,4-O-isopropylidene-α-D-ribo-hexofuranosonate 
• 392743-12-3 methyl 2,5-anhydro-6-O-benzyl-2-chloro-2-deoxy-3,4-O-isopropylidene-β-D-ribo-hexofuranosonate 
• 392743-20-3 2,5-anhydro-1,1-dichloro-1-deoxy-3,4-O-isopropylidene-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enitol 
• 392743-21-4 methyl 2,5-anhydro-2-chloro-3,4-O-isopropylidene-6-O-(4-methoxybenzyl)-β-D-ribo-2-hexulofuranosonate 
• 503610-46-6 methyl 2,5-anhydro-2-azido-6-O-benzyl-3,4-O-isopropylidene-α-D-ribo-hexulofuranosonate 

Relevant academic research and scientific papers

Identification of a fluorometabolite from Streptomyces sp. MA37: (2R3S4S)-5-fluoro-2,3,4-trihydroxypentanoic acid

(2R3S4S)-5-Fluoro-2,3,4-trihydroxypentanoic acid (5-FHPA) has been discovered as a new fluorometabolite in the soil bacterium Streptomyces sp. MA37. Exogenous addition of 5-fluoro-5-deoxy-d-ribose (5-FDR) into the cell free extract of MA37 demonstrated that 5-FDR was an intermediate to a range of unidentified fluorometabolites, distinct from fluoroacetate (FAc) and 4-fluorothreonine (4-FT). Bioinformatics analysis allowed identification of a gene cluster (fdr), encoding a pathway to the biosynthesis of 5-FHPA. Over-expression and in vitro assay of FdrC indicated that FdrC is a NAD+ dependent dehydrogenase responsible for oxidation of 5-FDR into 5-fluoro-5-deoxy-lactone, followed by hydrolysis to 5-FHPA. The identity of 5-FHPA in the fermentation broth was confirmed by synthesis of a reference compound and then co-correlation by 19F-NMR and GC-MS analysis. The occurrence of 5-FHPA proves the existence of a new fluorometabolite pathway.

Synthesis of α,ω-differently substituted cyclic ethers from carbohydrates by β-fragmentation of alkoxyl radicals

The β-fragmentation of alkoxyl radicals derived from easily available carbohydrates is a mild and efficient procedure to obtain unsymmetrical α,ω-disubstituted cyclic ethers.

A Chiral Synthesis of (+)-Lineatin, the Aggregation Pheromone of Trypodendron lineatum (Olivier), from D-Ribonolactone

Lineatin, the aggregation pheromone of Trypodendron lineatum (Olivier), has been shown to be (+)-(1R,4S,5R,7R)-3,3,7-trimethyl-2,9-dioxatricyclo4,7>nonane, (+)-1, by the first stereospecific chiral synthesis.D-Ribonolactone (3) was used to prepare (2S,3R)-2,3-(isopropylidenedioxy)-4-methyl-4-methoxy>pentanal (12).Condensation with the cyanophosphonate 7 provided two isomeric α,β-unsaturated nitriles, 13.Catalytic hydrogenation furnished (3RS,5R,6R)-3-cyano-5,6-(ispropylidenedioxy)-7-methyl-7-methxoy>-1,1-dimethoxyoctane (14), which, upon acid-catalyzed hydrolysis, produced the diastereoisomeric mixture 17.Blocking of the hemiacetal function of 17 with a tert-butyldimethylsilyl group, followed by reaction with methanesulfonyl chloride, produced the mixture 22.Acid-catalyzed cyclization of the deprotected hemiacetal 23 yielded (1R,4R,5R,7S)-7-cyano-3,3-dimethyl-4--2,9-dioxabicyclononane (24).Intramolecular nucleophilic ring closure provided (1R,4S,5R,7S)-7-cyano-3,3-dimethyl-2,9-dioxatricyclo4,7>nonane (25).Conversion of the cyano group to a methyl group using diisobutylaluminium hydride, followed by Wolff-Kishner reduction, produced (+)-1.This 16-step synthetic route to (+)-lineatin clearly established the absolute configuration as 1R,4S,5R,7R and produced (+)-lineatin in 2.7percent overall yield.

Design and synthesis of 2,6-disubstituted-4′-selenoadenosine- 5′-N,N-dimethyluronamide derivatives as human A3 adenosine receptor antagonists

A new series of 4′-selenoadenosine-5′-N,N-dimethyluronamide derivatives as highly potent and selective human A3 adenosine receptor (hA3AR) antagonists, is described. The highly selective A3AR agonists, 4′-selenoadenosine-5′-N-methyluronamides were successfully converted into selective antagonists by adding a second N-methyl group to the 5′-uronamide position. All the syn-thesized compounds showed medium to high binding affinity at the hA3AR. Among the synthe-sized compounds, 2-H-N6-3-iodobenzylamine derivative 9f exhibited the highest binding affinity at hA3AR. (Ki = 22.7 nM). The 2-H analogues generally showed better binding affinity than the 2-Cl analogues. The cAMP functional assay with 2-Cl-N6-3-iodobenzylamine derivative 9l demonstrated hA3AR antagonist activity. A molecular modelling study suggests an important role of the hydrogen of 5′-uronamide as an essential hydrogen bonding donor for hA3AR activation.

Discovery of a novel template, 7-substituted 7-deaza-4′-thioadenosine derivatives as multi-kinase inhibitors

The development of anticancer drugs remains challenging owing to the potential for drug resistance. The simultaneous inhibition of multiple targets involved in cancer could overcome resistance, and these agents would exhibit higher potency than single-target inhibitors. Protein kinases represent a promising target for the development of anticancer agents. As most multi-kinase inhibitors are heterocycles occupying only the hinge and hydrophobic region in the ATP binding site, we aimed to design multi-kinase inhibitors that would occupy the ribose pocket, along with the hinge and hydrophobic region, based on ATP-kinase interactions. Herein, we report the discovery of a novel 4′-thionucleoside template as a multi-kinase inhibitor with potent anticancer activity. The in vitro evaluation revealed a lead 1g (7-acetylene-7-deaza-4′-thioadenosine) with potent anticancer activity, and marked inhibition of TRKA, CK1δ, and DYRK1A/1B kinases in the kinome scan assay. We believe that these findings will pave the way for developing anticancer drugs.

High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues

A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.

Antioxidant composition comprising marliolide derivatives

The present invention relates to a marliolide derivative and an antioxidant composition containing the same as an active component, wherein the marliolide derivative increases the expression of a transcription factor Nrf2 that regulates the expression of an antioxidant-related protein without cytotoxicity, thereby increasing the expression of HO-1 and NQO1, which are antioxidant-related proteins. In addition, since the marliolide derivative is confirmed to inhibit the oxidation of DNA and lipids induced by TPA that induces oxidative stress, a composition containing the marliolide derivative can be provided as the antioxidant composition.(AA) Compound 1 (10 andmu;M)COPYRIGHT KIPO 2019

NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

Synthesis and biological evaluation of: N -arylated-lactam-type iminosugars as potential immunosuppressive agents

Since the immunosuppressive agents currently used in clinics have significant side effects, it is very important to search for new effective and safe immunosuppressants. Iminosugars as a new class of immunosuppressants are less explored. In this report, 24 new N-arylated iminosugar derivatives, including d-talo and d-galacto epimers, were designed and synthesized, and their immunosuppressive effects were evaluated by MTT assay. The experimental data demonstrated that compound 20 showed the strongest inhibition effect (IC50 = 6.94 μM). Further studies revealed that the inhibitory effects on splenocyte proliferation may come from the suppression of both IFN-γ and IL-4 cytokines. The preliminary structure-activity relationship (SAR) analysis suggested that N-arylated d-galacto-type iminosugars showed better inhibitory activities than d-talo-type analogues. The SAR analysis also showed that the inhibition effect of iminosugars can be improved by decreasing the polarity or increasing the hydrophobicity. These results may be beneficial to the discovery of new iminosugar derivatives as immunosuppressive agents.

Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar

The synthesis of a variety of chemically modified oligonucleotides requires the development of a practical synthetic method for its building block, i.e., nucleoside analogs. The one-pot Pummerer-like reaction using hypervalent iodine in combination with 6-chloropurine and an ‘armed’ 4-selenosugar bearing an electron-donating group at the 2-position gave the desired 4′-seleno-6-chloropurine derivative in higher yield as compared to the previous method using a ‘disarmed’ 4-selenosugar bearing an electron-withdrawing group at the 2-position. In addition, the use of 2,6-dichloropurine as a nucleobase transformable into guanine skeleton enabled an effective Pummerer-like reaction followed by isomerization to the desired N9 isomer under the acidic conditions. This Pummerer-like reaction between chlorinated purine bases and an ‘armed’ 4-selenosugar is advantageous because it affords 4′-selenopurine nucleosides in one-pot without the need for isolation of the unstable selenoxide derivative.