tert-butyl ((1R,3R,6S)-7-oxabicyclo[4.1.0]heptan-3-yl)carbamate

This intermediate takes 7-oxabicyclo[4.1.0]heptane as the core parent nucleus, with three chiral centers at positions 1, 3 and 6 with definite configurations. The carbon atom at position 3 is linked to a Boc-protected amino group; the Boc group can effectively protect the amino group from side reactions and can be selectively removed under mild acidic conditions (e.g., TFA/DCM system), meeting the requirements of downstream precise synthesis. The rigid structure of the oxabicyclic parent nucleus can provide a specific spatial conformation for downstream products and improve the matching degree with targets.

It has excellent solubility, easily soluble in common organic solvents such as dichloromethane, tetrahydrofuran and ethyl acetate, and slightly soluble in water. It is stable under room temperature and dry conditions, with the Boc group not easy to fall off, so high temperature (> 80°C), strong acid, strong base and direct strong light should be avoided. In terms of applications, it is mainly used as a core intermediate for chiral active pharmaceutical ingredient (API) synthesis, primarily applied in the synthesis of Lefamulin Acetate (a novel pleuromutilin antibiotic for the treatment of community-acquired bacterial pneumonia), while widely used in the R&D and production of other anti-infective, central nervous system and antiviral drugs. The chiral configuration directly determines the efficacy and selectivity of downstream drugs. Meanwhile, it can also be used for the preparation of chiral ligands to facilitate asymmetric catalytic reactions.

For industrial application, it requires chiral purity (ee value) ≥ 99% and chemical purity ≥ 98%. It should be sealed and stored in a dry, cool and well-ventilated place, separated from oxidants, acids and bases to prevent deterioration and ensure the effect of subsequent synthesis.