87894-27-7

Upstream product

• 186581-53-3 diazomethane 
• 187745-50-2 (-)-6-benzyloxy-3-hydroxyhexanoic acid 
• 158094-56-5 (+/-)-6-benzyloxy-3-hydroxyhexanoic acid ethyl ester 
• 5470-84-8 4-benzyloxybutanal 

Downstream Products

• 187745-51-3 (2R,3R)-6-benzyloxy-3-hydroxy-2-methyl-hexanoic acid methyl ester 
• 191352-08-6 (2R,3R)-6-benzyloxy-3-hydroxy-2-methyl-hexanoic acid hydrazide 

Relevant academic research and scientific papers

Total synthesis of the piperidinol alkaloid (-)-(2R,3R,6S)-cassine

A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral β-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine.

Enantiospecific Syntheses of Trifunctional (R)-3-Hydroxy Esters by Baker's Yeast Reduction

Asymmetric syntheses of the enantiomerically pure trifunctional (R)-3-hydroxy esters (7)-(10) can be achieved by baker's yeast reduction of the hydrolysed β-keto carboxylates (2)-(5) instead of by reduction of the corresponding esters.