171964-40-2

Upstream product

• 100-39-0 benzyl bromide 
• 62961-64-2 D-(-)-diisopropyl tartrate 

Downstream Products

• 430473-71-5 (E)-(2S,3R)-2,3-Bis-benzyloxy-6-methyl-hept-4-enal 
• 430473-70-4 (E)-(2R,3R)-2,3-Bis-benzyloxy-6-methyl-hept-4-en-1-ol 
• 1026450-96-3 (2S,3R)-2,3-Bis-benzyloxy-4-triisopropylsilanyloxy-butyraldehyde 
• 430473-68-0 (2R,3R)-2,3-Bis-benzyloxy-4-triisopropylsilanyloxy-butan-1-ol 
• 430473-69-1 ((E)-(2R,3R)-2,3-Bis-benzyloxy-6-methyl-hept-4-enyloxy)-triisopropyl-silane 
• 430473-72-6 (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester 
• 430473-73-7 (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide 
• 171863-60-8 (5R,6R)-5,6-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-methylhept-3-yn-2-ol 
• 171863-58-4 (3R,4R)-3,4-dibenzyloxy-1,1-dibromo-5-tert-butyldimethylsilyloxypent-1-ene 
• 171863-59-5 (((2R,3R)-2,3-bis(benzyloxy)pent-4-yn-1-yl)oxy)(tert-butyl)dimethylsilane 
• 162630-99-1 (2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal 
• 171622-74-5 (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol 
• 113350-84-8 (2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-butanediol 

Relevant academic research and scientific papers

Highly stereocontrolled total synthesis of (+)-bengamide E

Diisopropyl D-tartrate 7 was efficiently transformed into the hexacarbonyl dicobalt complexed aldehyde 23.A highly stereocontrolled aldol reaction of 23 with the O,S-acetal 20 in the presence of tin(IV) chloride provided, after decomplexation, the aldol adduct 21 as the sole product, which was subsequently converted into (+)-bengamide E 5.

Total synthesis of bengamide E

A total synthesis of bengamide E is reported. The synthesis includes the utilization of D-tartrate as the chiral building block, construction of the E-olefin by the Julia protocol, an anti-aldol reaction to generate C-2 and C-3 stereocenters, and coupling of the thioester with caprolactam hydrochloride using sodium 2-ethylhexanoate.