676342-57-7

Upstream product

• 87357-54-8 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose 
• 26597-74-0 1,2:5,6-di-O-isopropylidene-β-L-talofuranose 
• 81562-09-6 6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside 
• 26597-73-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2595-05-3 Diacetone D-glucose 
• 949586-02-1 6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-α-D-allofuranose 
• 32166-85-1 (S)-1-((3aR,5R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 29587-01-7 5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl methyl ether 
• 18968-50-8 1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 

Downstream Products

• 949586-03-2 C₂₆H₃₅O₅SiN₃ 

Relevant academic research and scientific papers

Ring-modified analogues and molecular dynamics studies to probe the requirements for fungicidal activities of malayamycin A and its N-nucleoside variants

(Chemical Equation Presented) The importance of functional group orientations and the integrity of the bicyclic perhydrofuran core of malayamycin A and two equally active N-nucleoside analogues as fungicides were investigated. Two analogues 10 and 11, representing a THP-truncated and a bicyclic aza-variant, were synthesized and found to be inactive. Molecular dynamics studies on malayamycin A and analogues were performed to highlight the importance of properly orientating the urea and methyl ether groups.

From D-Glucose to Biologically Potent L-Hexose Derivatives: Synthesis of α-L-Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate

A novel and convenient route for the synthesis of biologically potent and rare L-hexose derivatives from D-glucose is described. Conversion of diacetone-α-D-glucose (14) into 1,2:3,5-di-O-isopropylidene-β -L-idofuranose (19) was efficiently carried out in two steps. Orthogonal isopropylidene rearrangement of compound 19 led to 1,2:5,6-di-O-isopropylidene-β-L-idofuranose (27), which underwent regioselective epimerization at the C3 position to give the L-talo- and 3-functionalized L-idofuranosyl derivatives. Hydrolysis of compound 19 under acidic conditions furnished 1,6-anhydro-β-L-idopyranose (35) in excellent yield, which was successfully transformed into the corresponding L-allo, L-altro, L-gulo, and L-ido derivatives via regioselective benzylation, benzoylation, triflation and nucleophilic substitution as the key steps. Applications of these 1,6-anhydro-β-L-hexopyranoses as valuable building blocks to the syntheses of 4-methylcoumarin-7-yl-α-L-iduronic acid and the disaccharide moieties of bleomycin A2 as well as heparan sulfate are highlighted.