264186-63-2

Upstream product

• 264186-60-9 (-)-(E,4R,5S)-3-benzyl-5-(1-heptenyl)-4-methoxycarbonyloxazolidin-2-one 
• 264186-58-5 (-)-(E,4S,5S)-3-benzyl-4-cyano-5-(1-heptenyl)oxazolidin-2-one 
• 264186-56-3 (+)-(2R/S,3S,4E)-2-benzylamino-3-[(tert-butyldiphenylsilyl)oxy]dec-4-enenitrile 
• 264186-57-4 (+)-(2R/S,3S,4E)-2-benzylamino-3-hydroxydec-4-enenitrile 
• 264186-55-2 (+)-(2S,3E)-2-[(tert-butyldiphenylsilyl)oxy]non-3-enenitrile 
• 186087-75-2 (E)-(S)-2-Hydroxy-non-3-enenitrile 
• 2548-87-0 (E)-2-Octenal 

Downstream Products

• 264186-64-3 (-)-(4R,5R)-3-benzyl-5-formyl-4-methoxycarbonyloxazolidin-2-one 
• 264186-68-7 (-)-(E,4S,5S)-3-benzyl-5-(1-pentadecenyl)-4-(tri-iso-propylsilyloxymethyl)oxazolidin-2-one 
• 264186-65-4 (-)-(E,4R,5S)-3-benzyl-4-methoxycarbonyl-5-(1-pentadecenyl)oxazolidin-2-one 
• 264186-67-6 (-)-(E,4S,5S)-3-benzyl-4-(hydroxymethyl)-5-(1-pentadecenyl)oxazolidin-2-one 

Relevant academic research and scientific papers

A chemoenzymatic access to D- and L-sphingosines employing hydroxynitrile lyases

A chemoenzymatic access to D- or L-sphingosines is presented comprising of a total synthesis of the L-threo-isomer and formal syntheses of the other three isomers. Key to the development of a general synthetic strategy has been the use of enantiocomplementary hydroxynitrile lyases (Hnls) to yield an enantiomeric pair of starting materials. The (S)-Hnl from Hevea brasiliensis has been used to prepare L-threo-sphingosine in 14 steps and an overall 12% yield. Application of the (R)-Hnl from Prunus amygdaIus formally allows synthesis of D-threo- and D-erythro-sphingosines. (C) 2000 Elsevier Science Ltd.