109001-58-3

Upstream product

• 135056-64-3 (4aS,4bS,6R,8aR,10S,10aS)-10-Methoxy-2,4a-dimethyl-6-phenyl-3-trimethylsilanyl-4a,4b,8,8a-tetrahydro-4H-1,5,7,9-tetraoxa-phenanthren-10a-ol 
• 109001-55-0 methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-arabino-hexopyranoside-2-ulose 
• 43209-86-5 3-trimethylsilyl-3-buten-2-one 

Downstream Products

• 127910-93-4 Methyl 4,6-O-Benzylidene-2,3-dideoxy-3,2-C-<(3'R)-3'-hydroxybutan-1'-yl-4'-ylidene>-3-C-methyl-α-D-arabino-hexopyranoside 
• 135056-65-4 Methyl 3,2-C<(3'S)-3'-Benzoyloxybutan-1'-yl-4'-ylidene>-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-arabino-hexopyranoside 
• 127783-21-5 Methyl 4,6-O-Bezylidene-2,3-dideoxy-3,2-C-<(3'S)-3'-hydroxybutan-1'-yl-4'-ylidene>-3-C-methyl-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

Robinson Annulation on a Carbohydrate Derivative

The reactions of an enolate derived from methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose have been studied; examples of O-alkylation, C-alkylation and Robinson annulation were observed.In the latter case the structure of the product was confirmed by X-ray crystallography on a crystalline allylic alcohol prepared by reduction of the ketone produced in the reaction.

The First Example of a Robinson Annulation on a Carbohydrate Derivative

The stereocontrolled synthesis of a tricyclic carbohydrate derivative using the Robinson annulation on methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-arabino-hexapyranoside-2-ulose is reported.