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US 2025/0276992 A1Published application
Synthesis methods of acyl chain of qs-21 and derivative thereof
AssigneeObi Pharma, Inc.
InventorsMing-Tain LAI, Jhao-Long LIN, Wei-Han LEE, Bing-Cheng CHOU
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Abstract
The present disclosure provides synthesis methods used in the preparation of an acyl chain of QS-21 and its derivative.
Claims13
A method of preparing a compound of Formula I, comprising:
- (a) performing hydroxylation and esterification of L-isoleucine to obtain compound AC-2;
- (b) treating compound AC-2 by intramolecular epoxidation and addition of 1,3-dithiane with an inversion process to obtain compound AC-6;
- (c) installing a first alcohol protecting group to compound AC-6 and unmasking thio-protection to obtain Formula I-1
- (d) performing an aldol reaction of Formula I-1 with compound (S)-Aux. by SmI2 to obtain Formula I-2;
- (e) installing a second alcohol protecting group to Formula I-2 to obtain Formula I-3;
- and
- (f) removing the first alcohol protecting group from Formula I-3 via hydrogenolysis to obtain Formula I-4,
- wherein X1 is the first alcohol protecting group, and X2 is the second alcohol protecting group.
5 more elements
Dependencies are inferred from the claim text.