151130-45-9

Upstream product

• 6752-48-3 methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside 
• 64951-98-0 methyl 3-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside 
• 90761-25-4 methyl 3-O-benzyl-4,6-O-benzylideno-2-deoxy-α-D-ribo-hexoside 
• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 
• 151130-44-8 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-α-D-ribo-hexopyranoside 

Downstream Products

• 151130-47-1 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-4-O-methylsulfonyl-α-D-xylo-hexoside 
• 151130-46-0 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-α-D-xylo-hexopyranoside 
• 151130-44-8 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-α-D-ribo-hexopyranoside 

Relevant academic research and scientific papers

The Synthesis of Some Pyrrolidines as Potential Precursors to Retronecine

Methyl β-D-galactopyranoside was converted into methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside, but subsequent transformation of the anomeric centre into a dithioacetal was unsatisfactory. Alternatively, methyl β-D-galactopyranoside easily gave methyl 4-azido-3,6-di-O-benzyl-2,4-dideoxy-β-D-arabino-hexoside, and this could be transformed by a reductive amination into two pyrrolidines as potential precursors to retronecine. Related chemistry gave (4S,5S,6R)-6-benzyloxy-4-benzyloxymethyl-3-oxa-1-azabicyclooctan-2-one, the structure of which was confirmed by a single-crystal X-ray structure determination. Finally, the synthesis of a potential precursor to heliotridine (an epimer of retronecine), namely methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-α-D-ribo-hexoside, from methyl α-D-mannopyranoside is reported.