73111-63-4Relevant academic research and scientific papers
Chiron Approach for the Total Synthesis of Brevipolide M
Liu, Yang,Zhao, Ziyang,Hu, Chao,Zhao, Chuanfang,Liu, Jun,Du, Yuguo
, p. 478 - 482 (2022/02/23)
An efficient stereoselective synthesis of brevipolide M was established in 13 linear steps and 17.8% overall yields based on chiron approach. The key steps of our synthesis involved tandem Wittig olefination tetrahydrofuran cyclization and sequential ring
Aflexible synthesis of cyclopentitol derivatives based on ring-closing metathesis of carbohydrate-derived 1,6-dienes
Ovaa, Huib,Lastdrager, Bas,Codee, Jeroen D. C.,Van der Marel, Gijs A.,Overkleeft, Herman S.,Van Boom, Jacques H.
, p. 2370 - 2377 (2007/10/03)
Four partially protected stereoisomeric cyclopentenetriols 5, 10, 15 and 21 have been prepared by ring-closing metathesis of carbohydrate-derived 1,6-dienes. The presence of a differentiated allylic alcohol in the cyclopentenetriols allows a variety of synthetic transformations, underlining the synthetic use of the prepared cyclopentenetriol derivatives as chiral building blocks.
The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides
Mereyala, Hari Babu,Goud, P. Mallikarjun,Gadikota, Rajendrakumar Reddy,Maddala, Rama Krishna,Reddy, K. Ramasubba
, p. 1201 - 1210 (2007/10/03)
Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.
A stereoselective and efficient route to (3S, 4R, 5S)-(+)-4,5- dihydroxycyclopent-1-en-3-ylamine: The side chain of the hypermodified nucleoside Q
Ovaa, Huib,Codee, Jeroen D. C.,Lastdrager, Bas,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Van Boom, Jacques H.
, p. 7987 - 7990 (2007/10/03)
A stereoselective and high yielding route is described to a suitably protected derivative of (3S, 4R, 5S)-(+)-3-amino-4,5-dihydroxycyclopent-1- ene, the side chain moiety of queuosine. The synthetic route comprises a ring-closing metathesis (RCM) of a mannofuranose-derived diene followed by Overman rearrangement.
