111425-50-4

Upstream product

• 627-40-7 methylallylether 
• 111425-52-6 thiophenyl 2,3-dideoxy-α-D-glucopyranoside 
• 116-11-0 2-Methoxypropene 
• 108-98-5 thiophenol 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 

Relevant academic research and scientific papers

Alkylation and Acylation of Phenylthio 2,3-Dideoxyhex-2-enopyranosides at the Anomeric Centre by Polarity Inversion

Alkylation and acylation of phenylthio 2,3-dideoxy-α-D erythro-hex-2-enopyranoside derivatives at the anomeric centre by polarity inversion give C-1 alkylated or acylated phenylthio 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides.

Photo amidoglycosylation of an allal azidoformate. Synthesis of beta-2-amido allopyranosides.

[figure: see text] Photolysis of an allal C-3 azidoformate provoked intramolecular nitrene insertion into the glycal C=C unit and allowed direct incorporation of alcohol nucleophiles as beta-disposed substituents at C-1. The 2-amido allopyranoside product

Organotransition metal modified sugars: Part 22. Direct metalation of glycals: Short and efficient routes to diversely protected stannylated glycals

A complete set of D-hexose-derived silyl and isopropylidene/silyl-protected glycals bearing complementary configurations at C-3 and C-4 has been synthesized in short and efficient 1-3 step sequences from standard precursors. The glycals have been applied to metalation reactions to give storable vinyl lithium equivalents by subsequent transmetalation to vinyl stannanes which represent valuable intermediates for transition metal-catalyzed cross-coupling reactions. A 1H-NMR-assisted conformational analysis has been carried out with the protected glycals and the stannylated congeners. The isopropylidene/silyl-protected glycals adopt the 4H5-conformation caused by the bicyclic system, whereas the conformations of the fully silyl-protected monocyclic glycals are mainly controlled by the vinylogous anomeric effect. The discussed galactal- and allal-derivatives show dynamic behaviour on the NMR-time-scale. At low temperatures the two possible conformers (4H5 and 5H4) have been observed demonstrating competition of steric congestion and stereoelectronic interaction via the vinylogous anomeric effect (VAE).