30725-00-9

Basic information

• Product Name: 2,3-O-Isopropylidene-D-ribonic gamma-lactone
• Synonyms: 2,3-O-ISOPROPYLIDENE-D-RIBONIC ACID GAMMA LACTONE;2,3-O-ISOPROPYLIDENE-D-RIBONIC GAMMA-LACTONE;2,3-O-ISOPROPYLIDENE-D-RIBONO-1,4-LACTONE;2,3-ISOPROPYLIDENE-D-RIBONO-1,4-LACTONE;2,3-ISOPROPYLIDENE-D-RIBONOLACTONE;ISOPROPYLIDENE-D-RIBONOLACTONE;2,3-o-isopropylidene-d-ribonic γ-lactone;D-Ribonic acid, 2,3-O-(1-methylethylidene)-, .gamma.-lactone
• CAS NO: 30725-00-9
• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.18
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 30725-00-9.mol
• Article Data: 68

Chemical Properties

• Melting Point: 135-139 °C
• Boiling Point: 243.17°C (rough estimate)
• Flash Point: 139.7 °C
• Appearance: White to Off-white/Powder
• Density: 1.2069 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4348 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Soluble in methanol at 50mg/ml, acetone, dichloromethane, ethyl
• PKA: 13.68±0.10(Predicted)
• Water Solubility: soluble
• BRN: 10090
• CAS DataBase Reference: 2,3-O-Isopropylidene-D-ribonic gamma-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O-Isopropylidene-D-ribonic gamma-lactone(30725-00-9)
• EPA Substance Registry System: 2,3-O-Isopropylidene-D-ribonic gamma-lactone(30725-00-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 30725-00-9(Hazardous Substances Data)

Usage

Description

2,3-Isopropylidene-D-ribonolactone is a building block. It has been used in the stereocontrolled synthesis of the carbohydrates 6-epi-trehazolin and 6-epi-trehalamine.

Chemical Properties

White Crystalline Solid

Uses

2,3-O-Isopropylidene-D-ribonic acid-1,4-lactone is used for the synthesis of C-nucleosides, prostanoids and GABA analogs via homochiral 2-piperidones. It is the starting material for the preparation of biochemical compounds including C-nucleosides, such as neplanocin A, and GABA analogs, via homochiral 2-piperidones.

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

• 77-76-9 2,2-dimethoxy-propane 
• 5336-08-3 D-Ribono-1,4-lactone 
• 75-05-8 acetonitrile 
• 328533-43-3 2,3-O-isopropylidene-1-O-pivaloyl-α-D-ribofuranose 
• 67-64-1 acetone 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 50-69-1 D-ribose 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 157453-65-1 (3R,4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxy-dihydrofuran-2-one 
• 67814-68-0 2,3-O-isopropylidene-β-D-ribofuranose 
• 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 

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 
• 336110-47-5 (S)-2-[((3aR,4R,6aR)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-(2-nitro-benzenesulfonyl)-amino]-4-methyl-pentanoic acid methyl ester 
• 807363-14-0 (3aR,6S,6aR)-6-(Hydroxy-methoxy-methyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 99315-76-1 (5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone 
• 103233-14-3 (4S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-methyldihydrofuran-2(3H)-one 
• 138946-55-1 (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol 
• 138946-45-9 5-bromo-2,3-O-isopropylidene-2,3,4-trihydroxypentanal-O-benzyl oxime 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 99315-75-0 (-)-5-O-(diphenyl-t-butylsilyl)-2,3-O-(thiocarbonyl)-D-ribono-1,4-lactone 
• 121687-49-8 3-C-ethyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-erythro-pentono-1,4-lactone 
• 121687-50-1 3-C-propyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-erythro-pentono-1,4-lactone 
• 121687-51-2 3-C-butyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-erythro-pentono-1,4-lactone 
• 155300-64-4 (1R,2R,3S,4R)-4-Benzyloxyamino-cyclopentane-1,2,3-triol 

Relevant articles and documents

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.

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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.

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.

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