1361469-71-7

Upstream product

• 108-24-7 acetic anhydride 
• 118968-02-8 (1S)-(1,3/2,4)-1,2-dibenzyloxy-3-hydroxy-4-hydroxymethylcyclohex-5-ene 
• 219623-01-5 2,3,4,6-tetra-O-acetyl-1-deoxy-1-methylene-5a-carba-D-glucopyranose 
• 219622-93-2 (S)-4-((4R,5S)-5-Ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-5-trimethylsilanylmethyl-[1,3]dioxan-5-ol 
• 219622-91-0 (S)-4-((4R,5S)-5-Ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-[1,3]dioxan-5-one 
• 117275-40-8 1,2-dideoxy-3,4:5,7-bis-O-(1-methylethylidene)-D-gluco-hept-1-ynitol 
• 97747-53-0 (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate 
• 1361469-70-6 C₁₅H₂₂O₉ 
• 1027746-05-9 (1R,2S,3R,4R)-4-[(acetyloxy)methyl]-6-oxocyclohexane-1,2,3-triyl triacetate 

Relevant academic research and scientific papers

Synthesis of Carba-Cyclophellitols: a New Class of Carbohydrate Mimetics

Cyclophellitol and cyclophellitol aziridine are potent and irreversible inhibitors of retaining β-glucosidases. They preferentially adopt a 4H3 half-chair conformation, thereby mimicking the substrate-transition-state conformation characteristic of retaining β-glucosidases. As a consequence, both compounds bind tightly to the enzyme active site, and attack of the catalytic nucleophile onto the epoxide/aziridine results in enzyme deactivation. Replacement of the epoxide oxygen in cyclophellitol by a (substituted) carbon yielded carba-cyclophellitols, a conceptually new class of inhibitors of retaining β-glucosidases, as we demonstrated in a recent communication. In this paper, in-depth synthetic studies of this class of compounds are described, and the preparation of a comprehensive set of structurally and configurationally new carba-cyclophellitols is presented.

Synthetic strategies directed towards 5a-carbahexopyranoses and derivatives based on 6-endo-trig radical cyclizations

Several synthetic strategies directed towards 5a-carbahexopyranoses and based on 6-endo-trig radical cyclization of unsaturated carbohydrate derivatives have been devised. Three elements for regiocontrol to optimize the 6-endo/5-exo ratio have been incorporated, and their efficiencies in directing 6-endo cyclizations have been evaluated. These elements - namely: i) the incorporation of a substituent at C-5 (radical numbering), ii) the use of a vinyl (rather than alkyl) radical, and iii) the inclusion of ring strain in the system - have proved useful when used in combination. The simultaneous presence of two of them also results in 6-endo selectivity. On another topic, the ozonation of the ensuing alkenylstananes to afford diols seems to be based on a tin-oxygen rearrangement, similar to that reported for related vinylsilanes, rather than on remarkable stabilities of tin-containing primary ozonides as we had previously suggested.