19684-32-3

Basic information

• Product Name: 1,2-O-Isopropylidene-5-keto-α-D-glucose
• Synonyms: 1,2-O-Isopropylidene-5-keto-α-D-glucose;2-hydroxy-1-((3aR,5S,6S)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanone
• CAS NO: 19684-32-3
• Molecular Formula: C₉H₁₄O₆
• Molecular Weight: 218.20386
• Product Categories: Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 19684-32-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-O-Isopropylidene-5-keto-α-D-glucose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-Isopropylidene-5-keto-α-D-glucose(19684-32-3)
• EPA Substance Registry System: 1,2-O-Isopropylidene-5-keto-α-D-glucose(19684-32-3)

Safety Data

• Hazardous Substances Data: 19684-32-3(Hazardous Substances Data)

Usage

Chemical Properties

Beige Solid

Uses

1,2-O-Isopropylidene-5-keto-α-D-glucose is a reactant used in organic synthesis of D-glucose derivatives as potential antimalarial agents and inhibitors of several glucosidases.

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 253328-56-2 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 29747-91-9 1,2-O-isopropylidene-β-L-idofuranose 
• 28069-98-9 Acetic acid (3aR,6S,6aR)-5-((R)-1,2-diacetoxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Relevant articles and documents

Synthesis and Antiproliferative Activities of Novel Substituted 5-Anilino-α-Glucofuranose Derivatives

In order to find novel antitumor candidate agents with high efficiency and low toxicity, 14 novel substituted 5-anilino-α-glucofuranose derivatives have been designed, synthesized and evaluated for antiproliferative activities in vitro. Their structures were characterized by NMR (1H and 13C) and HR-MS, and configuration (R/S) at C(5) was identified by two-dimensional 1H,1H-NOESY-NMR spectrum. Their antiproliferative activities against human tumor cells were investigated by MTT assay. The results demonstrated that most of the synthesized compounds had antiproliferative effects comparable to the reference drugs gefitinib and lapatinib. In particular, (5R)-5-O-(3-chloro-4-{[5-(4-fluorophenyl)thiophen-2-yl]methyl}anilino)-5-deoxy-1,2-O-(1-methylethylidene)-α-glucofuranose (9da) showed the most potent antiproliferative effects against SW480, A431 and A549 cells, with IC50 values of 8.57, 5.15 and 15.24 μm, respectively. This work suggested 5-anilino-α-glucofuranose as an antitumor core structure that may open a new way to develop more potent anti-cancer agents.

N-Thiocarbonyl iminosugars: Synthesis and evaluation of castanospermine analogues bearing oxazole-2(3H)-thione moieties

A straightforward and efficient synthetic route to a new class of glycosidase inhibitors containing an oxazole-2(3H)-thione moiety has been devised. The approach involves the formation of α-hydroxy ketones, which, after condensation with thiocyanic acid, leads to the formation of the heterocycle. By exploiting the ability of the nitrogen atom of oxazoline-2-thione precursors to act as nucleophiles in intramolecular addition, castanospermine analogues could be readily prepared in good overall yields. Glycosidase inhibitory activity compared to oxazolidinethione analogues showed a strong influence of the double bond, for example with pseudoiminosugar 19, by suppressing α-glucosidase inhibition and introducing, to a moderate level, β-glucosidase inhibitory activity. Reactivities showed the propensity of oxazole-2(3H)-thiones - especially when fused on carbohydrate frames - to convert into 1,3-oxazolidine-2-thione aminals through nucleophilic addition to the double bond, leading to unexpected tricyclic structure 21. Oxazole-2(3H)-thione moieties have been anchored onto carbohydrates in a five-step sequence that allows access to castanospermine analogues. Copyright

Expeditious synthesis of azasugars by the double reductive amination of dicarbonyl sugars

Polyhydroxylated pyrrolidines and piperidines were prepared by the double reductive amination of dicarbonyl sugars with primary amines and NaCNBH3 in MeOH. Stereocontrol in these reactions depended on the nature of the amine and dicarbonyl sugar. For example, 5-keto-D-fructose (7) gave three pyrrolidine stereoisomers, with the N-alkylated 2,5-anhydro-2,5-imino-D-glucitol predominating. Under similar reaction conditions with benzhydrylamine, 5-keto-D-glucose (20) afforded a 96:4 mixture of piperidines favoring D-gluco 25A, whereas 5-keto-D-mannose (6) produced a 67:33 mixture enriched in D-manno isomer 40. This method allowed for the direct and relatively short synthesis of 1-deoxynojirimycin (DNJ, 1) and 1-deoxymannojirimycin (DMJ, 5) and N-alkylated derivatives thereof. Similar reactions with O-protected 5-keto-D-glucose derivatives 21 and 22 were less stereoselective and lower yielding.