146404-45-7Relevant academic research and scientific papers
Base Catalyzed Degradations of Rapamycin
Steffan, Robert J.,Kearny, Robert M.,Hu, David C.,Failli, Amedeo A.,Skotnicki, Jerauld S.,et al.
, p. 3699 - 3702 (1993)
The base catalyzed degradation of rapamycin was re-examined and a sequence of steps involving β-elimination, retro-aldol cleavage and benzilic acid rearrangement occur leading to several new products.
Degradation of rapamycin: Synthesis of a rapamycin derived fragment containing the tricarbonyl and triene sectors
Yohannes,Myers,Danishefsky
, p. 2075 - 2078 (1993)
A degradation of rapamycin involving retro-Michael and retro-aldol steps retrieves the entire C1-C27 subunit.
Efficient removal of pipecolinate from rapamycin and FK506 by reaction with n-Bu4N+CN-
Luengo, Juan I.,Rozamus, Leonard W.,Holt, Dennis A.
, p. 4599 - 4602 (2007/10/02)
The reaction of rapamycin (1) and FK506 (11) with n-Bu4N+CN- / aq. THF results in an efficient excision of their pipecolinate subunits, leading in good yields to compounds 3 and 12, respectively. Two sequential ring cleava
Studies on the chemistry of rapamycin: Novel transformations under Lewis-acid catalysis
Luengo,Konialian,Holt
, p. 991 - 994 (2007/10/02)
The reactivity of rapamycin under mild Lewis-acid catalysis has been investigated. The molecule has been found to be extremely sensitive to basic reagents due to carboxylate elimination β to the C24 ketone. However, transformations normally eff
DEGRADATION OF RAPAMYCIN: RETRIEVAL OF MAJOR INTACT SUBUNITS.
Yohannes, Daniel,Danishefsky, Samuel J.
, p. 7469 - 7472 (2007/10/02)
The degradation of rapamycin has made available key substructures which have defined the structures of advanced synthetic intermediates.
