19684-32-3

Usage

Uses

Used in Pharmaceutical Industry:
1,2-O-Isopropylidene-5-keto-α-D-glucose is used as a reactant in the organic synthesis of D-glucose derivatives. These derivatives have potential applications as antimalarial agents, offering new treatment options for malaria.
Additionally, these D-glucose derivatives are used as inhibitors of several glucosidases. Glucosidase inhibitors play a crucial role in modulating the activity of enzymes that break down complex carbohydrates, which can be beneficial in managing certain metabolic disorders and conditions related to carbohydrate metabolism.

Upstream product

• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-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 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 132198-14-2 N-Benzhydryl-1-deoxynojirimycin 
• 132198-14-2 (2S,3R,4R,5S)-1-Benzhydryl-2-hydroxymethyl-piperidine-3,4,5-triol 
• 72599-27-0 N-butyldeoxynojirimycin 
• 79206-22-7 N-Dodecyl-1-deoxynojirimycin 

Relevant academic research and scientific papers

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-aryl-1-deoxynojirimycin derivative and application thereof in preparing of medicine for treating diabetes

The invention discloses an N-aryl-1-deoxynojirimycin derivative and application thereof in preparing of medicines for treating diabetes. The structural formula of the derivative is as shown in the specification, and in the formula, R1 is halogen or C1-C4 alkyl; R2 is substituted aryl; R3 is H or acyl with 1-4 atoms. The compound disclosed by the invention has functions of remarkably reducing blood sugar and promoting discharge of glucose from urea, and can be used for preparing medicines for treating diabetes.

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.

Regioselective mono-oxidation of Non-protected carbohydrates by brominolysis of the tin intermediates

Most of the glycosides examined were smoothly oxidized by the bis-tributyltin oxide-bromine method without protection of the other hydroxyl groups to the mono-oxo derivatives in high yield and with high regioselectivity.The regioselectivity (position of oxidation) can be predicted from two independent rules: anomeric control (the oxidation takes place at C-3 for the glycosides which have an equatorial glycosidic linkage and at C-4 for those which have an axial glycosidic linkage) and axial oxidation for cis-1,2 glycols.Keywords - carbohydrate; glycoside; oxidation; regioselective oxidation; bis-tributyltin oxide-bromine; dibutyltin oxide-bromine; brominolysis; oxo-glycoside; 13C-NMR.

PRACTICAL SYNTHESIS OF NOJIRIMYCIN

The short step and efficient synthesis of nojirimycin (1) from commercially available 1,2-isopropylidene-D-glucofuranose (2) was described.Oxidation of 2 with (Bu3Sn)2O-Br2 followed by oximation, isomerization, and stereoselective reduction gave the 5-amino derivative of gluco-configuration (6a), which was converted to nojirimycin bisulfite adduct (8) in 50percent overall isolated yield.

BROMINE OXIDATION OF 1,2-O-ISOPROPYLIDINE-α-D-GLUCOFURANOSE AND SUCROSE

Sucrose and 1,2-O-isopropylidene-α-D-glucofuranose (1) were oxidised with bromine in aqueous solution at pH 7 and room temperature.The resulting keto derivatives were converted into their more-stable O-methyloximes, which were characterised by spectroscopic and chromatographic methods.Oxidation of 1 occured at C-3 and C-5, with a preference for C-5.In the sucrose derivatives isolated after oxidation, those having a keto group in the glucopyranosyl moiety preponderated.The axial fructofuranosyl aglycon protects position 3 in the glucopyranosyl group and oxidation occurs only at C-2 and C-4.Small amounts of sucrose oxidised at C-3 in the fructofuranosyl moiety were also found.