175415-06-2

Upstream product

• 203795-15-7 (S)-3-{(R)-2-[(S)-(4-Benzyloxy-phenyl)-(4-methoxy-phenylamino)-methyl]-5-phenyl-pentanoyl}-4-phenyl-oxazolidin-2-one 
• 20371-41-9 5-phenylvaleric acid chloride 
• 157435-14-8 (S)-4-Phenyl-3-(5-phenyl-pentanoyl)-oxazolidin-2-one 

Downstream Products

• 190448-74-9 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 190448-70-5 (3R,4S)-1-(4-Methoxy-phenyl)-3-(3-phenyl-propyl)-4-[4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-azetidin-2-one 
• 208259-80-7 (3R,4S)-1-(4-Methoxy-phenyl)-3-(3-phenyl-propyl)-4-[4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-phenyl]-azetidin-2-one 
• 190448-65-8 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 175415-07-3 (3R,4S)-4-(4-Hydroxy-phenyl)-1-(4-methoxy-phenyl)-3-(3-phenyl-propyl)-azetidin-2-one 

Relevant academic research and scientific papers

Carboxy-substitutes 2-azetidinones as cholesterol absorption inhibitors

Metabolism initiated SAR studies led to the discovery of a new class of potent 2-azetidinone cholesterol absorption inhibitors. These studies found that a heteroatom at the para position of the C-4 phenyl ring is not a requirement for cholesterol absorption inhibition as was suggested by earlier findings. Substitution of Ph-linker-COOR for PhOMe at the C-4 position enhanced absorption inhibition.

Sugar-substituted 2-azetidinones as cholesterol absorption inhibitors

The asymmetric synthesis of a glucuronide conjugate of the 2-azetidinone cholesterol absorption inhibitor Sch 48461 was accomplished to confirm the structure of a metabolite isolated from in vivo sources. Key features of this article include the asymmetric synthesis of 2-azetidinones by Evan's chiral oxazolidinone methodology and glucuronide formation by a Mitsunobu protocol.