329361-79-7Relevant academic research and scientific papers
A highly expeditious synthesis of a bicyclic iminosugar using the novel key step of [NMM]+[HSO4]- promoted conjugate addition and Mitsunobu reaction
Prasad, Virendra,Kumar, Dhananjay,Tiwari, Vinod K.
, p. 5794 - 5797 (2013/05/21)
A simple and highly facile protocol has been developed for the stereoselective synthesis of 1-deoxy-norcastanospermine from readily available d-glucose. N-Methylmorpholinium hydrogen sulphate was seen for the first time as a suitable catalyst for the faci
Conjugate addition of amines to sugar derived olefinic esters: Synthesis of glycosylated amino esters as DNA topoisomerase-II inhibitors
Khan,Tripathi,Tiwari,Mishra,Reddy,Saxena
, p. 591 - 604 (2007/10/03)
Conjugate addition of amines to olefinic esters derived from sugars leading to formation of glycosylated amino esters in a stereoselective manner is described. Some of the synthesized compounds possess DNA topoisomerase-II enzyme inhibitory activities at low concentrations.
Synthesis of glycosylated β-amino acids as new class of antitubercular agents
Tripathi,Tripathi,Tiwari,Bala, Laxmi,Sinha,Srivastava,Srivastava,Srivastava
, p. 773 - 781 (2007/10/03)
A series of glycosylated β-amino acids was prepared and evaluated against Mycobacterium tuberculosis, M. avium, M. fortuitum and M. smegmatis. The compounds were designed to mimic the enzyme D-alanine racemase and glycosyl transferase involved in the bios
Intermolecular Michael addition of substituted amines to a sugar-derived α,β-unsaturated ester: Synthesis of 1-deoxy-D-gluco- and -L-ido-homonojirimycin, 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine
Patil,Tilekar,Dhavale
, p. 1065 - 1074 (2007/10/03)
The synthesis of polyhydroxylated piperidine alkaloids, namely, 1-deoxy-D-gluco-homonojirimycin 3a, 1-deoxy-L-ido-homonojirimycin 3b, and indolizidine alkaloids 1-deoxy-castanospermine 5a and 1-deoxy-8a-epi-castanospermine 5b, has been achieved. The key step involved is the intermolecular Michael addition of benzylamine to α,β-unsaturated ester 1, derived from D-glucose, which afforded diastereomeric mixture of β-amino esters 6a and 6b with D-gluco- and L-ido- configuration at C5, respectively. Attempts were made to increase and/or alter the diastereoselectivity at the newly generated stereocenter. The high stereoselectivity, in favor of L-ido-isomer 6b, was achieved under kinetically controlled conditions by using lithium N-benzyl amide as a Michael donor. The β-amino esters 6a and 6b represent common intermediates to target molecules. Thus, LAH reduction of 6a and 6b, individually, gave β-amino alcohol 7a and 7b. Sequential hydrogenolysis, selective protection of the amino group, followed by hydrolysis of the 1,2-acetonide functionality, and hydrogenation gave 3a and 3b, respectively. On the other hand, the β-amino ester 6a was converted to γ-amino ester 13a by Arndt-Eistert synthesis, which on hydrogenolysis and treatment with sodium acetate gave γ-lactam 14a. The LAH reduction afforded pyrrolidene. The N-protection-hydrolysis-hydrogenation cascade successfully executed, and 1-deoxy-castanospermine 5a was obtained in good yield. The same sequence of reactions was applied to β-amino ester 6b, which afforded 1-deoxy-8a-epi-castanospermine 5b.
Stereocontrolled 1,3-addition reaction of silyl ketene acetal to sugar nitrone: Synthesis of D-gluco-homo-1-deoxynojirimycin and L-ido-homo-1-deoxynojirimycin
Saha, Nabendu N,Desai, Vijaya N,Dhavale, Dilip D
, p. 39 - 46 (2007/10/03)
The 1,3-addition reaction of silyl ketene acetal 6 to D-glucose derived nitrone 7 followed by reductive cleavage of the N-O bond afforded D-gluco- and L-ido-β-amino ester derivatives of 9a and 9b. The diastereoselectivity in addition reaction was improved
