131589-20-3

Upstream product

• 116661-41-7 (2S,4R,5R)-1-(benzyloxy)-5-hydroxy-2,4,6-trimethylhept-6-en-3-one 
• 77-76-9 2,2-dimethoxy-propane 
• 106357-31-7 (2S,3S,4R)-1-benzyloxy-2,4-dimethylhex-5-ene-3-ol 
• 108867-45-4 (2S,3S,4R)-2,4-dimethyl-hex-5-ene-1,3-diol 
• 131589-19-0 (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol 
• 131722-56-0 (2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal 
• 131589-18-9 (2S,3S,4R)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4-dimethyl-5-hexene-1,3-diol 
• 100-39-0 benzyl bromide 
• 116546-78-2 (S)-1-benzyloxy-2-methylpentan-3-one 
• 131589-43-0 (3R,4S,5R,6S)-7-Benzyloxy-2,4,6-trimethyl-hept-1-ene-3,5-diol 

Downstream Products

• 131681-65-7 (2S,3R,4S,5R,6S,7R,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 
• 131681-74-8 (2S,3R,4S,5R,6S,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 
• 131589-27-0 (2S,3R,4S,5R,6R,7R,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 
• 131681-73-7 (2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 
• 209974-51-6 C₄₆H₇₄O₉SSi 
• 131617-19-1 (3R,4S,5R,6S)-7-(benzyloxy)-3,5-(isopropylidenedioxy)-4,6-dimethylheptan-2-one 

Relevant academic research and scientific papers

Total asymmetric synthesis of a new 9,12-anhydroerythronolide aglycone

Two novel, potentially antimicrobial erythronolide aglycon analogs ((-)-9 and (-)-30, respectively), which incorporate a large number of contiguous stereogenic centers, have been prepared by multistep synthesis from simple chirons. The chemistry presented demonstrates the power of the so-called 'naked sugars of the second generation' approach. As for the sporeamicins, our macrolides are 9,12-anhydroerythronolides, yet presenting a higher degree of complexity due to additional functional groups.

Total asymmetric synthesis of Seco-acids of 9,12 anhydroerythronolide aglycons

The Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'S)- camphanate was converted into (2R,3R,4S,5S,6R,7R)-3,6-epoxy-4,5- isopropylidenedioxy-2,4,6-trimethyl-7-[(tert-butyl)-dimethylsilylloxy]non-I- yl phenyl sulfoxides (6), the condensation of which with (3R,4S,5R,6S)-7- benzyloxy-3,5-isopropylidenedioxy-4,6-dimethylheptan-2-one (7) led to the partially-protected seco-acid of the 9,12-anhydroerythronolide aglycon (5).