74850-75-2

Upstream product

• 74850-77-4 Toluene-4-sulfonic acid (3aR,5S,6aR)-6-[1-cyano-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 
• 4376-01-6 sodium diphenylphosphide 
• 74850-78-5 3-<(E)-cyanomethylene>-3-deoxy-1,2-O-isopropylidene-5-O-tosyl-α-D-xylofuranose 
• 74850-77-4 3-<(Z)-cyanomethylene>-3-deoxy-1,2-O-isopropylidene-5-O-tosyl-α-D-xylofuranose 
• 20514-01-6 1,2-O-isopropylidene-5-O-p-toluenesulfonyl-α-D-erythro-ketofuranos-3-ulose 
• 6893-65-8 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 

Downstream Products

• 74850-76-3 C-((2S,2aR,2bS,5aR,6aR)-2a-Diphenylphosphanyl-4,4-dimethyl-hexahydro-3,5,6-trioxa-cyclobuta[a]pentalen-2-yl)-methylamine 
• 103476-62-6 (1R,3R,4S,5R,6R)-6-aminomethyl-5-diphenylphosphino-3,4-O-isopropylidene-2-oxabicyclo(3.2.0)heptane-3,4-diol 

Relevant academic research and scientific papers

Syntheses of Novel Sugar Phosphine Derivatives, and Homogeneous Hydrogenation Reaction with Their Rhodium Complexes

Optically active diphenylphosphine derivatives, (1R,3R,4S,5R,6R)-6-cyano-5-diphenylphosphino-3,4-O-isopropylidene-2-oxabicycloheptane-3,4-diol (15) and its reduction product (17), were prepared by the cyclization of 12 or 13, which was obtained from a common sugar, D-glucose.These phosphines were used as ligands in the rhodium complex-catalyzed asymmetric hydrogenation of prochiral olefins.The rhodium complex catalyst which was constructed with 2 mol of 15 and 1 mol of rhodium(cyclooctene)2Cl (20) worked efficiently for the asymmetric hydrogenation of α-acetamidocinnamic acid (18) and itaconic acid (24) with 91.6percent ee-(S) and 69.6percent ee-(R), respectively.On the other hand, the rhodium complex constructed with 1 mol of 17 and 1 mol of 20 was less effective than that of 15, giving 39.0percent ee-(R) in the reaction with 18.Methyl esters of 18 and 24 were also hydrogenated using the complex of 15.Keywords - D-glucose; (1R,3R,4S,5R,6R)-6-cyano-5-diphenylphosphino-3,4-O-isopropylidene-2-oxabicycloheptane-3,4-diol; cyclobutane ring formation; chiral phosphine ligand; rhodium complex; asymmetric hydrogenation; enantioselectivity

ASSYMETRIC HYDROGENATION WITH CHIRAL PHOSPHINE LIGAND HAVING C-PPh2 BONDING DERIVED FROM D-GLUCOSE

Rh-complex of 6S-cyano-5R-diphenylphosphino-3R,4S-O-isopropylidene-2-oxa-bicycloheptane showed the relatively high enantioselectivity (S-configuration) in the hydrogenation of α-acetamidocinnamic acid, whereas Rh-complex of the 6S-aminomethyl compo