89755-42-0Relevant articles and documents
Stereoselective construction of 2,8-dioxabicyclo[3.3.1]nonane/nonene systems from 3-C-branched glycals
Reddy, Gadi Madhusudhan,Sridhar, Perali Ramu
, p. 1496 - 1504 (2014/03/21)
A stereoselective approach for the formation of 2,8-dioxabicyclo[3.3.1] nonane/nonene frameworks through the formation of 3-C-branched glycals encompassing the Claisen rearrangement of the carbohydrate-derived allyl-vinyl ethers and TMSOTf-catalyzed acetalization reactions as key steps is revealed. A novel acetalization of 3-C-branched glycals with a tentative mechanism is proposed. The expedient protocol is evaluated by synthesizing a number of 2,8-dioxabicyclo[3.3.1]nonane/nonene architectures. An efficient, stereoselective intramolecular acetalization of 3-C-branched glycal derivatives to provide 2,8-dioxabicyclo[3.3.1]nonane/nonene frameworks is described. The generality of the reaction is investigated and a plausible mechanism is postulated. Copyright
Stereoselective Construction of 2,8-Dioxabicyclo[3.3.1]nonane/nonene Systems from 3-C-Branched Glycals
Reddy, Gadi Madhusudhan,Sridhar, Perali Ramu
, p. 1496 - 1504 (2015/10/05)
A stereoselective approach for the formation of 2,8-dioxabicyclo[3.3.1]nonane/nonene frameworks through the formation of 3-C-branched glycals encompassing the Claisen rearrangement of the carbohydrate-derived allyl-vinyl ethers and TMSOTf-catalyzed acetalization reactions as key steps is revealed. A novel acetalization of 3-C-branched glycals with a tentative mechanism is proposed. The expedient protocol is evaluated by synthesizing a number of 2,8-dioxabicyclo[3.3.1]nonane/nonene architectures.
Stereoselective synthesis of cis-fused perhydrofuro[2,3-b]furan derivatives from sugar-derived allyl vinyl ethers
Sridhar, Perali Ramu,Reddy, Gadi Madhusudhan,Seshadri, Kalapati
, p. 6228 - 6235 (2013/01/15)
A stereoselective methodology has been developed for the construction of cis-fused perhydrofuro[2,3-b]furans, via 3-C-branched glycal derivatives, involving Claisen rearrangement of sugar-derived allyl vinyl ethers, followed by a one-pot ozonolysis and acid-mediated acetalization. The methodology was used for the stereoselective synthesis of the P2 ligand in the recently FDA approved HIV protease inhibitor darunavir (Prezista). The methodology was also successfully used for the synthesis of cis-fused perhydro-5-oxofuro[2,3-b] furan derivatives.