923592-14-7

Upstream product

• 100-39-0 benzyl bromide 
• 1053608-61-9 (4S)-[(1R,2S,3S,4S)-1,2,4-tris(benzyloxy)-3-[(2-trimethylsilylethoxy)methoxy]-6-(tert-butyldiphenylsilyloxy)hexyl]-2,2-dimethyl-1,3-dioxolane 
• 1054673-08-3 (1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol 
• 1054617-61-6 (2S,4R,5S,6S)-6-O-benzyl-8-O-(tert-butyldiphenylsilyl)-1,2-di-O-isopropylidene-4-O-(triethylsilyl)-1,2,4,5,6,8-hexahydroxyoctan-3-one 
• 914638-70-3 (S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanol 
• 914638-64-5 (S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanal 

Downstream Products

• 923592-16-9 (1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine 
• 923592-15-8 (3S,4S,5S,6S,7S)-3,5,6-tris(benzyloxy)-8-tert-butoxyoctane-1,4,7-triyl tris(methanesulfonate) 

Relevant academic research and scientific papers

Stereoselective synthesis of the glycosidase inhibitor australine through a one-pot, double-cyclization strategy

(Chemical Equation Presented) A stereocontrolled, convergent synthesis of the alkaloid australine, a glycosidase inhibitor of the pyrrolizidine class, is described. The chiral starting materials were ketone 3, derived from L-erythrulose, and α-alkoxy aldehyde 4, prepared from L-malic acid. A key step of the synthesis was the highly stereoselective aldol reaction between 4 and a Z boron enolate derived from 3. Another key step was the one-pot construction of the bicyclic pyrrolizidine system by means of a three-step sequence of SN2 displacements induced by benzylamine on a trimesylate precursor.