1450899-53-2

Upstream product

• 1450899-50-9 C₁₉H₃₄O₃Si 
• 96013-95-5 3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde 
• 1450899-47-4 (S)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-5-(3-(tertbutyldimethylsilyloxy)phenyl)-2-methylpentane-1,5-dione 
• 1450899-51-0 (2S,5S)-5-(3-(tert-butyldimethylsilyloxy)phenyl)-5-methoxy-2-methylpentanal 
• 123-38-6 propionaldehyde 
• 1450899-48-5 (R)-4-benzyl-3-((2S,5S)-5-(3-(tert-butyldimethylsilyloxy)-phenyl)-5-hydroxy-2-methylpentanoyl)oxazolidin-2-one 
• 1450899-49-6 (R)-4-benzyl-3-((2S,5S)-5-(3-(tert-butyldimethylsilyloxy)-phenyl)-5-methoxy-2-methylpentanoyl)oxazolidin-2-one 

Downstream Products

• 1450899-59-8 (2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoic acid 
• 1450899-61-2 (2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate 
• 1224952-48-0 (+)-(2R,3R,4S,7S)-3-(((3R,4R)-3,4-dihydroxypentanoyl)oxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoic acid 
• 1450899-63-4 (2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate 

Relevant academic research and scientific papers

Total synthesis of nhatrangin a

A concise and stereoselective approach for the synthesis of key intermediates for aplysiatoxins, oscillatoxins, and nhatrangins and their utility for the total synthesis of nhatrangin A has been demonstrated. The advanced intermediates aromatic aldehyde 11 and dihydroxy acid 12 were synthesized in eight steps (44% overall yield) and three steps (55% overall yield), respectively. An asymmetric Michael addition, CBS reduction, and proline-catalyzed crossed-aldol reactions were utilized as key steps for the generation of all the chirality of main chain hydroxyaldehyde, while the appended side-chain-protected 3,4-dihydroxypentanoic acid was achieved in a shortest route, using Sharpless dihydroxylation, diol protection, and RuO 4-catalyzed aromatic over-oxidation reactions. Synthesis of nhatrangin A was accomplished by coupling of dihydroxy acid 12 with β-hydroxyallyl ester (obtained from 11) under Yamaguchi reaction conditions followed by a one-pot deprotection of all protecting groups.