1221741-79-2

Upstream product

• 1360566-51-3 C₂₄H₄₀N₂O₆Si 
• 1221741-69-0 C₂₄H₄₂N₂O₅Si 
• 1221741-71-4 C₃₂H₄₈N₂O₇Si 
• 1221741-73-6 C₃₂H₅₀N₂O₆Si 
• 1221741-75-8 C₄₃H₆₈N₄O₁₀Si 
• 179549-00-9 C₁₁H₁₃NO₄ 
• 501-53-1 benzyl chloroformate 
• 1221741-77-0 C₄₃H₆₆N₄O₉Si 

Downstream Products

• 1360566-57-9 C₃₅H₄₈N₆O₉ 
• 1360566-59-1 C₃₅H₄₆N₆O₁₀ 
• 1360566-61-5 C₃₇H₄₈N₆O₁₁ 
• 1360566-63-7 C₂₈H₄₁N₇O₉ 
• 1360566-64-8 C₂₈H₃₉N₇O₁₀ 
• 1360599-65-0 C₂₆H₄₀N₄O₇ 
• 1360603-28-6 C₄₅H₅₆N₆O₁₂ 
• 1360566-56-8 C₄₃H₅₄N₆O₁₁ 

Relevant academic research and scientific papers

Synthesis of skeletal analogues of saxitoxin derivatives and evaluation of their inhibitory activity on sodium ion channels NaV1.4 and Na V1.5

Skeletal analogues of saxitoxin (STX) that possess a fused-type tricyclic ring system, designated FD-STX, were synthesized as candidate sodium ion channel modulators. Three kinds of FD-STX derivatives 4 a-c with different substitution at C13 were synthesized, and their inhibitory activity on sodium ion channels was examined by means of cell-based assay. (-)-FD-STX (4 a) and (-)-FD-dcSTX (4 b), which showed moderate inhibitory activity, were further evaluated by the use of the patch-clamp method in cells that expressed NaV1.4 (a tetrodotoxin-sensitive sodium channel subtype) and NaV1.5 (a tetrodotoxin-resistant sodium channel subtype). These compounds showed moderate inhibitory activity towards NaV1.4, and weaker inhibitory activity towards NaV1.5. Uniquely, however, the inhibition of Na V1.5 by (-)-FD-dcSTX (4 b) was "irreversible".

Total synthesis of (+)-decarbamoylsaxitoxin and (+)-gonyautoxin 3

Figure presented Facile construction of the complex saxitoxin (STX) skeleton is carried out by using a novel, conformationally controlled, guanidine cyclization process that relies on the use of neighboring group participation. The utility of this methodology is verified by its employment in syntheses of both natural and unnatural STX derivatives.

Total synthesis of (-)- and (+)-decarbamoyloxysaxitoxin and (+-)-saxitoxin

Enantioselective total syntheses of (-)- and (-1-)-decarbamoyloxysaxitoxin (doSTX) and (-l-)-saxitoxin (STX) were achieved. The characteristic spiro-fused cyclic guanidine structure of STX was constructed by oxidation at the C4 position with IBX via an α-iminium carbonyl intermediate and acid-promoted cyclization of guanidine at the C5 position. A second-generation methodology was developed for the synthesis of STX, featuring discriminative reduction of the nitro group and N-O bond in nitroisoxazolidine. This approach provides efficient access to the key diamine intermediate for STXs.