17231-20-8

Upstream product

• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 818-08-6 di(n-butyl)tin oxide 
• 128-08-5 N-Bromosuccinimide 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 1203587-46-5 ethyl 3-O-benzyl-5,6-dideoxy-5-C-hydroxymethyl-1,2-isopropylidene-α-D-xylo-hept-5-(E)-enofuranuronate 
• 1203587-51-2 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-threo-furanos-4-yl)pyridazin-6-one 
• 1203587-52-3 ethyl 4-(3-O-benzyl-1,2-O-isopropylidene-α-D-threo-furanos-4-yl)-1-phenylpyrazole-3-carboxylate 
• 1418874-33-5 5-(1′H-benzo[1′,2′,3′]triazol-1′-yl)-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 1418874-34-6 5-(2′H-benzo[1′,2′,3′]triazol-2′-yl)-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 1013026-69-1 C₁₇H₁₉NO₅S 
• 1197004-06-0 C₁₇H₂₂N₂O₅ 
• 1197004-02-6 5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

Oxidation of stannylene derivatives of carbohydrates using 1,3-dibromo-5,5-dimethylhydantoin

1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) has been used to oxidize stannylene derivatives of monosaccharides to give hydroxy-ketones thereof. Oxidations could be performed rapidly and in good-to-excellent yields. The oxidizing reagent DBDMH thus provides

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

Synthesis of pseudo-C-nucleosides from β-formyl-α,β- unsaturated ester bearing a β-furanosidic moiety

Pseudo-C-nucleosides have potential biological activity, and an efficient synthesis of new pseudo-C-nucleosides has been developed via the reaction of a β-formyl-α,β-unsaturated ester bearing a β-sugar moiety with hydrazines in neutral and acidic conditio

Synthesis and biological evaluation of sugars containing α,β-unsaturated γ-lactones

The stereocontrolled synthesis of new sugar derivatives carrying the α,β-unsaturated δ-lactone (butenolide) moiety is described. Sugar-fused or sugar-linked butenolides can be constructed by an efficient reaction sequence involving Wittig olefination of 3- or 5-keto sugars and intramolecular cyclization of the intermediate γ-hydroxy α,β-unsaturated esters. The antimicrobial activities of the products and that of a known sugar-derived pyranoid α,β-unsaturated δ-lactone were investigated against six pathogenic bacteria and six fungi. The pyranoid α,β-unsaturated δ-lactone 29 proved to be the most active compound in this series towards the plant pathogenic fungi Colletotrichum coffeanum (coffee berry disease) and Pyricularia oryzae (rice blast disease). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.