20672-64-4Relevant academic research and scientific papers
A novel and environmental friendly synthetic route for hydroxypyrrolidines using zeolites
Fan,Chuah,Jaenicke, Stephan
, p. 103 - 114 (2018/12/13)
A critical step in the synthesis of the hydroxypyrrolidines, 1,4-dideoxy-1,4-imino-L-lyxitol and 1,4-dideoxy-1,4-imino-D-lyxitol, from the corresponding D-sugars is the synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses. Instead of applying homogeneous catalysis process with conventional inorganic acid catalysts like HCl and HClO4, it was found that heterogeneous catalysis using zeolites could be used for the one-pot synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses directly from D-sugars, MeOH and acetone at mild condition. The best catalyst was H-beta zeolite containing a Si/Al molar ratio of 150, where a yield of >83% was obtained. The overall yields of the five-step procedure to 1,4-dideoxy-1,4-imino-L-lyxitol and 1,4-dideoxy-1,4-imino-D-lyxitol were 57% and 50%, respectively. This synthetic procedure has several advantages such as competitive overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the zeolite catalyst can be easily recovered from the reaction mixture and reused with no loss of activity.
Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization
Mohanrao, Raja,Asokan, Aromal,Sureshan, Kana M.
, p. 6707 - 6710 (2014/06/23)
We report a bio-inspired, strain driven epimerization of trans-ketals to cis-ketals through an enolate intermediate. Swern oxidation of a hydroxyl group adjacent to a trans-ketal effects both oxidation and its epimerization to cis-ketal. This novel and general strategy allows inversion of up to three contiguous stereocenters and has been illustrated by the synthesis of several unnatural/rare isomers of carbohydrates/cyclitols from their naturally abundant isomers. This journal is the Partner Organisations 2014.
Improved syntheses of d-ribo- and 2-deoxy-d-ribofuranose phospho sugars from methyl β-d-ribopyranoside
Hanaya, Tadashi,Koga, Yuko,Kawamoto, Heizan,Yamamoto, Hiroshi
experimental part, p. 581 - 591 (2009/09/08)
Abstract - Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-13-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-13-D-etythro-pentopyranoside (20) were efficiently prepared respectively from methyl2,3-O-isopropylidene-[3-D-rib
