124476-95-5

Upstream product

• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 116-11-0 2-Methoxypropene 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 

Downstream Products

• 1092981-89-9 1-deoxy-2,3:4,6-di-O-isopropylidene-1-[(Rs)-phenylsulfinyl]-β-D-galactopyranoside 
• 1092981-97-9 1-deoxy-2,3:4,6-di-O-isopropylidene-1-[(Ss)-phenylsulfinyl]-β-D-galactopyranoside 

Relevant academic research and scientific papers

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).

PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULPHONES

Phenyl thioglycopyranosides with various protecting groups (acetal, ether, ester) underwent reductive lithiation at C-1, followed by rapid elimination of the 2-substituent, when treated with lithium naphthalenide in tetrahydrofuran at low temperature.Thus

CONVENIENT SYNTHESES OF SUBSTITUTED PYRANOID GLYCALS FROM THIOPHENYL GLYCOSIDES AND GLYCOSYL PHENYLSULFONES

A series of substituted thiophenyl glycosides and glycosyl phenylsulfones were converted in high yield into glycals after reductive lithiation with lithium naphthalenide, followed by elimination of the substituent at C-2.