219967-36-9

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 219967-35-8 (2S,3R,4R,5S,6S)-1-acetoxy-4-benzyloxy-6,7-O-isopropylidenedioxy-5-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 219967-24-5 (2S,6S)-6-tert-butyldimethylsiloxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4,5-bis(methoxymethyloxymethyl)-6H-pyran-3(2H)-one 
• 219967-27-8 (2S,3R,4R,5R,6S)-6-tert-butyldimethylsiloxy-3-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)] 
• 219967-22-3 (2S,3S)-3-{2'-[3',4'-bis(methoxymethyloxymethyl)furyl]}-1,2-O-isopropylideneglycerol 
• 219967-29-0 (2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)] 
• 219967-30-3 (2S,3R,4R,5R,6R)-3-benzyloxy-6-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)] 
• 219967-26-7 (2S,4S,5R,6S)-6-tert-butyldimethylsiloxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-3-one-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)] 
• 219967-25-6 (2S,4S,5R,6S)-6-tert-butyldimethylsiloxy-4,5-dihydroxy-4,5-bis(methoxymethyloxymethyl)-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-3-one 
• 219967-34-7 (2R,3R,4R,5S,6S)-4-benzyloxy-6,7-O-isopropylidenedioxy-1,5-heptanediol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 882523-27-5 (2S)-6-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4,5-bis(methoxymethyloxymethyl)-6H-pyran-3(2H)-one 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 219967-21-2 3,4-bis(methoxymethyloxymethyl)furan 
• 100-39-0 benzyl bromide 

Downstream Products

• 219967-37-0 (2R,3R,4R,5S,6S)-4-benzyloxy-5-tert-butyldimethylsiloxy-6,7-O-isopropylidenedioxy-1-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 882523-29-7 (2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 882523-28-6 (2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-8-nonyne-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 882523-30-0 (2S,3S,4R,5R,6S,7R)-1,7-diacetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-2-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 219967-38-1 (2R,3R,4R,5S,6S)-4-benzyloxy-5-tert-butyldimethylsiloxy-6,7-O-isopropylidenedioxypentanal-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 219967-42-7 (2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 219967-40-5 (2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-8-nonyn-7-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 219967-41-6 (2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-7-methoxymethyloxy-8-nonyne-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 219967-39-2 (2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-7-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 219967-43-8 (2S,3S,4R,5R,6S,7R)-1-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-2-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 
• 219967-44-9 (3R,4R,5R,6S,7R)-1-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-2-one-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 

Relevant academic research and scientific papers

Synthesis of dioxabicyclo[3.2.1]octane core of the zaragozic acids

Synthesis of the bicyclic core of zaragozic acids employing chiral furylglycerol (6) is described. Key steps are stereoselective construction of the C4 to C6 carbon centers by syn-dihydroxylation of alkene followed by reduction of carbonyl group in pyrano

Construction of the zaragozic acids core bicycle

Concise synthesis of the bicyclic core of zaragozic acids has been accomplished by the utilization of (2S, 3S)-furylglycerol 7. The key features are based on the diastereoselective dihydroxylation of enone 8 followed by reduction of ketone 11 to control the stereochemistries at the C4-C6 positions of the target molecule. Addition of lithium trimethylsilylacetylide to aldehyde 20 provided propargyl alcohol 21, which was further transformed into the bicyclic core 25, a potent intermediate for the synthesis of zaragozic acids.