Mal-(1R,2S,3R,4S)-himic acid-alkyne 

Mal-(1R,2S,3R,4S)-himic acid-alkyne is a trifunctional click chemistry scaffold containing complementary functionalities for copper catalyzed azide-alkyne (CuAAC), thiol-Michael addition, and inverse electron demand Diels-Alder (iEDDA) click reactions^[1].

Mal-(1R,2S,3R,4S)-himic acid-alkyne (Compound 3) undergoes highly selective CuAAC click chemistry at its alkyne group, with >99% conversion to the triazole product in individual reactions and full conversion within 1 h in a sequential one-pot setup, with minimal side product formation^[1].
Mal-(1R,2S,3R,4S)-himic acid-alkyne undergoes highly selective thiol-Michael click chemistry at its maleimide group, with >99% conversion to the thioether product in individual reactions and complete consumption in a sequential one-pot setup, with low levels of norbornene-directed side product formation^[1].
Mal-(1R,2S,3R,4S)-himic acid-alkyne undergoes highly selective iEDDA click chemistry at its norbornene double bond, with >99% conversion to dihydropyridazine/pyridazine products in individual reactions and complete consumption in a sequential one-pot setup, with reaction rate dependent on solvent choice^[1].
Mal-(1R,2S,3R,4S)-himic acid-alkyne undergoes simultaneous one-pot triple click chemistry resulting in <10% yield of the targeted triple-click product, as copper catalyst deactivation inhibits the CuAAC reaction despite quantitative completion of iEDDA and thiol-Michael reactions^[1].
Mal-(1R,2S,3R,4S)-himic acid-alkyne undergoes sequential one-pot triple click chemistry, performed in the order CuAAC, iEDDA, thiol-Michael, resulting in >99% conversion to the targeted triple-click product with 95% isolated yield, with complete selective consumption of all three clickable functional groups and no detectable side reactions^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

343.33

C₁₈H₁₇NO₆

2032454-73-0

O=C(OCC#C)[C@H]1[C@@H](C(OCCN(C(C=C2)=O)C2=O)=O)[C@H]3C=C[C@@H]1C3

Room temperature in continental US; may vary elsewhere.

Please store the product under the recommended conditions in the Certificate of Analysis.

• [1]. Knall AC, et al. A trifunctional linker suitable for conducting three orthogonal click chemistries in one pot. Org Biomol Chem. 2016;14(45):10576-10580.  [Content Brief]