132273-07-5Relevant academic research and scientific papers
Cholic Acid as an Architectural Component in Biomimetic/Molecular Recogition Chemistry; Synthesis of "Cholaphanes" With Facial Differentiation of Functionality
Bonar-Law, Richard P.,Davis, Anthony P.,Dorgan, Brian J.
, p. 9855 - 9866 (2007/10/02)
Facially-differentiated cholaphanes (2) were synthesized in good yields from cholic acid (1).Key steps were the selective 3,7-bis-O-acetylation of methyl cholate (3), the 12-O-benzylation of diacetate 4, and the introduction of a 3β-(p-aminomethyl)phenyl substituent using an arylmanganese reagent and employing the novel ''benzostabase'' N-protection methodology.
The "benzostabase" protecting group for primary amines; application to aliphatic amines
Bonar-Law,Davis,Dorgan,Reetz,Wehrsig
, p. 6725 - 6728 (2007/10/02)
The "benzostabase" (BSB) protecting group has been applied to primary aliphatic amines. It can be introduced via a dehydrogenative silylation employing an air- and moisture-stable reagent, and is appreciably more acid-stable than the related "stabase" group. BSB protection has been used in a stereoselective synthesis of amino-alcohols involving the addition of organometallic reagents to protected amino-aldehydes under "non-chelation control".
