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US 2022/0033428 A1Published application
Large scale preparation of pseudo-trisaccharide aminoglycosides and of intermediates thereof
AssigneeEloxox Pharmaceuticals Ltd.
InventorsMichael MIZHIRITSKII, Mani Bushan KOTALA, Ravinder PALADI
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Abstract
Synthetic pathways for preparing pseudo-trisaccharide aminoglycoside compounds represented by Formula I or Ia as defined in the specification and donor and acceptor compounds useful for preparing such compounds are provided. A process of stereoselectively preparing compounds represented by Formula III as defined in the specification, while avoiding chromatographic separation of stereoisomers are also provided. Compounds prepared by the described processes and uses thereof are also provided.
Claims14
A process of preparing a compound represented by Formula III:
- wherein:
- OT1 and OT2 are each independently a protected hydroxyl group;
- R8 is alkyl;
- and
- D is a protected amino group,
- the process comprising:
- reacting a compound represented by Formula IIIa:
- with a Grignard reagent represented by a Formula R8MgX, wherein X is halide, to thereby obtain stereoselectively a compound represented by Formula IIIb:
- converting said compound represented by Formula IIIb to a compound represented by Formula IIIc:
- reacting said compound represented by Formula IIIc with an amino-protecting group to thereby form said D;
- and
- reacting said compound represented by Formula IIIc with hydroxy protecting groups to thereby form said OT1 and OT2,
- thereby preparing the compound represented by Formula III.
10 more elements
Dependencies are inferred from the claim text.