247145-68-2

Upstream product

• 247145-67-1 (2R,3R,6S)-6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-2H-pyran-3-ol 
• 81389-87-9 (2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol 
• 100-51-6 benzyl alcohol 
• 2873-29-2 D-glucal triacetate 
• 247145-65-9 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol 
• 69247-18-3 benzyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside 

Relevant academic research and scientific papers

Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA

The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.

Synthesis of amino-sugars using the directed dihydroxylation reaction

The synthesis of protected forms of two amino-sugars, talosamine 1 and allosamine 2, is described; the syn, syn stereochemistry at C-2, C-3 and C-4 was controlled by the use of a hydrogen-bonding directed dihydroxylation reaction using stoichiometric and catalytic OsO4; proof of the relative stereochemistry of the allosamine series was obtained through an X-ray crystal structure of a protected derivative.