681830-34-2

Upstream product

• 681830-24-0 (R)-4-Benzyl-3-((2R,3S,4R,6R)-2-benzyloxy-3-hydroxy-4-methyl-6-triethylsilanyloxy-heptanoyl)-oxazolidin-2-one 
• 681830-33-1 (2R,4R)-2-methyl-4-(trimethylsilyloxy)pentan-1-ol 
• 681830-17-1 (2R,4R)-2-Methyl-4-triethylsilanyloxy-pentanal 
• 994-30-9 triethylsilyl chloride 
• 75-08-1 ethanethiol 
• 681830-31-9 (R)-4-Benzyl-3-((2R,3S,4R,6R)-2-benzyloxy-4-methyl-3,6-bis-triethylsilanyloxy-heptanoyl)-oxazolidin-2-one 

Relevant academic research and scientific papers

Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

The efficient synthesis of the C(19)-C(26) subunit of amphidinolide B(1) and B(2) has been completed using a boron-mediated aldol reaction. The synthesis of the C(19)-C(26) subunit of amphidinolide B(3) has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.