158665-65-7Relevant academic research and scientific papers
Asymmetric Synthesis of Pentono- and 6-Deoxyhexono-δ-lactams via Hetero-Diels-Alder Reactions with Nitroso Dienophile
Defoin, Albert,Sarazin, Herve,Sifferlen, Thierry,Strehler, Christiane,Streith, Jacques
, p. 1417 - 1428 (2007/10/03)
Asymmetric Diels-Alder reaction of the pentadienoic and hexadienoic acids 2a,b with the chiral chloronitroso derivative 3 gave the primary adducts 4a,b with good-to-excellent enantioselectivity. Subsequent cis- or trans-dihydroxylation and hydrogenolytic cleavage of the N-O bond led to the 5-amino-5-deoxypentono-δ-lactams 13a, 14, 15a, and 16 in the D-ribose, L-arabinose, D-xylose, and L-lyxose series, respectively, and to the 5-amino-5,6-dideoxyhexono-δ-lactams 13b and 15b in the D-allose and D-glucose series, respectively.
De novo asymmetric synthesis of two 5-amino-5,6-dideoxy-D-allose derivatives
Defoin, Albert,Sarazin, Herve,Strehler, Christiane,Streith, Jacques
, p. 5653 - 5656 (2007/10/02)
Diels-Alder cycloaddition of sorbic aldehyde derivative 9 and of sorbic acid 10 with the chiral chloro-nitroso dienophile 7 led with excellent regio- and diastereoselectivity to the chiral cycloadducts 11a and 12, respectively. Catalytic osmylation of their Bzl-derivatives 11b and 13b, followed by reductive cleavage of the N-O bonds, gave ultimately the chiral aminoallose derivatives D-5 and D-6 which are potential glycosidase inhibitors.
