Oxazolidines are weaker bases (pKa 6–7) than parent β-amino alcohols and found to be more lipophilic than the parent compound at physiological pH.Name: (4R,4’R)-2,2′-Cyclopropylidenebis(4,5-dihydro-4-phenyloxazole) For example, the oxazolidine prodrug of phenylephrine prepared from pivaldehyde has penetrated the cornea much more easily than the parent drug as a result of increased lipophilicity.
Name: (4R,4’R)-2,2′-Cyclopropylidenebis(4,5-dihydro-4-phenyloxazole)In 2018, Bhattarai, Bijay;Nagorny, Pavel published 《Enantioselective Total Synthesis of Cannogenol-3-O-α-L-rhamnoside via Sequential Cu(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions》. 《Organic Letters》published the findings. The article contains the following contents:
A concise and scalable enantioselective total synthesis of the natural cardenolides cannogenol and cannogenol-3-O-α-L-rhamnoside has been achieved in 18 linear steps. The synthesis features a Cu(II)-catalyzed enantioselective and diastereoselective Michael reaction/tandem aldol cyclization and a one-pot reduction/transposition, which resulted in a rapid (6 linear steps) assembly of a functionalized intermediate containing C19 oxygenation that could be elaborated to cardenolide cannogenol. In addition, a strategy for achieving regio- and stereoselective glycosylation at the C3 position of synthetic cannogenol was developed and applied to the preparation of cannogenol-3-O-α-L-rhamnoside. And (4R,4’R)-2,2′-Cyclopropylidenebis(4,5-dihydro-4-phenyloxazole) (cas: 1819994-24-5) was used in the research process.
Oxazolidines are weaker bases (pKa 6–7) than parent β-amino alcohols and found to be more lipophilic than the parent compound at physiological pH.Name: (4R,4’R)-2,2′-Cyclopropylidenebis(4,5-dihydro-4-phenyloxazole) For example, the oxazolidine prodrug of phenylephrine prepared from pivaldehyde has penetrated the cornea much more easily than the parent drug as a result of increased lipophilicity.
Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem