121194-85-2

Upstream product

• 117122-84-6 (2R,4S,5R)-2-phenyl-5-hydroxy-1,3-dioxane-4-methanol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 874620-24-3 1,3-O-benzylidene-2-O-[(S-methylthio)thiocarbonyl]-4-O-(tert-butyldimethylsilyl)-L-erythritol 
• 121194-89-6 (6R,7R,8S,8aR,2'R,4'S,5'R)-(+)-4'-(t-butyldimethylsiloxymethyl)-2'-phenyl-1',3'-dioxan-5'-yl 6,7-bis-(3,4-dimethoxyphenyl)-5-oxoindolizidine-8-carboxylate 
• 121194-89-6 (6S,7R,8S,8aR)-6,7-Bis-(3,4-dimethoxy-phenyl)-5-oxo-octahydro-indolizine-8-carboxylic acid (2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-[1,3]dioxan-5-yl ester 
• 121213-14-7 (E)-6-[(E)-2,3-Bis-(3,4-dimethoxy-phenyl)-acryloylamino]-hex-2-enoic acid (2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-[1,3]dioxan-5-yl ester 
• 121194-87-4 (Triphenyl-λ⁵-phosphanylidene)-acetic acid (2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-[1,3]dioxan-5-yl ester 
• 390408-53-4 1,3-O-benzylidene-4-O-(tert-butyldimethylsilyl)-2-deoxy-L-erythritol 
• 121194-86-3 (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate 

Relevant academic research and scientific papers

ASYMMETRIC TOTAL SYNTHESES OF (-)-TYLOPHORINE VIA THE HIGHLY ENANTIOSELECTIVE INTRAMOLECULAR DOUBLE MICHAEL REACTION

Asymmetric total synthesis of (-)-tylophorine (2) was achieved with a high enantioselectivity through the intramolecular double Michael reaction of the α , β -unsaturated ester (8) having a novel chiral auxiliary with tert.-butyldimethylsilyl trifluoromethanesulfonate and Et3N.

Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring α-glucosidase inhibitor, salacinol (1a), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-d- arabinitol (3), with cyclic sulfates (8, 9, and 10), and their α-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents for the α-glucosidase inhibitory activity. A practical synthetic route to 3 starting from d-xylose is also described.

Asymmetric Total Synthesis of Naturally Occurring (R)-(-)-Enantiomer of Tylophorine via Intramolecular Double Michael Reaction

The first asymmetric total synthesis of the naturally occurring (R)-(-)-enantiomer (1) of tylophorine was achieved with high enantioselectivity via the intramolecular double Michael reaction of α,β-unsaturated esters (10) and (20), having two different chiral auxiliaries, with t-butyldimethylsilyl trifluoromethanesulphonate in the presence of triethylamine. (-)-Phenylmenthol and (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-5-hydroxy-2-phenyl-1,3-dioxane, readily available from D-glucose, were used as chiral auxiliaries.