151130-22-2

Upstream product

• 63592-79-0 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside 
• 14897-47-3 methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 
• 55331-65-2 methyl 4,6-O-benzylidene-2-deoxy-β-D-lyxo-hexoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 3971-46-8 methyl 2-deoxy-β-D-lyxo-hexopyranoside 
• 151130-20-0 methyl 3,4-O-isopropylidene-2-O-(methylthio)thiocarbonyl-β-D-galactoside 
• 151130-21-1 methyl 2-deoxy-3,4-O-isopropylidene-β-D-lyxo-hexoside 
• 119093-27-5 methyl 2-deoxy-4,6-O-para-methoxybenzylidene-β-D-lyxo-hexoside 
• 104530-15-6 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 

Downstream Products

• 82300-39-8 methyl 3-O-benzyl-2-deoxy-6-O-triphenylmethyl-D-ribohexopyranoside 
• 106444-96-6 Dithiocarbonic acid O-((2R,3S,4S,6S)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester 
• 106444-95-5 Dithiocarbonic acid O-((2R,3S,4S,6R)-4-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl) ester S-methyl ester 
• 151130-24-4 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-β-D-lyxo-hexopyranoside 
• 151183-18-5 methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside 
• 151130-26-6 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-4-O-methylsulfonyl-β-D-lyxo-hexoside 

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.