1400879-07-3

Upstream product

• 124-41-4 sodium methylate 
• 1400879-04-0 benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside 
• 1320337-31-2 benzyl 4,6-di-O-acetyl-2,3-dideoxy-3-ethylthio-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

2,3-Unsaturated enoses. A Pummerer rearrangement route to sugar vinyl sulfides and synthesis of 3-deoxy-3-alkyl/arylsulfinyl pyranosides

A Pummerer rearrangement of 2,3-dideoxy-3-alkyl/arylsulfinyl-arabino- hexopyranosides is reported. Treatment of sulfinyl-arabino-hexopyranoside derivatives, obtained through oxidation of the corresponding thio-derivatives, with trifluoroacetic anhydride (TFAA)/pyridine led to a facile formation of 2,3-dideoxy-3-alkyl/arylthio-hex-2-enopyranosides. Upon conversion of sugar vinyl sulfides to vinyl sulfoxides, conjugate addition reactions were conducted with alkoxides, to afford 3-deoxy-3-alkyl/arylsulfinyl pyranosides, in the manno-configuration exclusively. Whereas the conjugate addition reaction did not proceed with ether protecting groups, ester protecting groups and free hydroxyl groups in the sugar vinyl sulfoxide permitted the reaction.