185155-53-7

Upstream product

• 15890-72-9 laurylmagnesium bromide 
• 85960-55-0 (S)-(2-phenylmethoxyethyl)oxirane 
• 6278-91-7 4-(benzyloxy)-2-butanone 
• 143-15-7 1-dodecylbromide 
• 185155-56-0 4-benzyloxy-1-bromo-butan-2-one 
• 185155-48-0 4-benzyloxy-1-hydroxybutan-2-one 
• 100-44-7 benzyl chloride 
• 82780-39-0 (S)-4-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane 
• 71998-69-1 (S)-4-benzyloxy-1,2-butanediol 

Downstream Products

• 1140968-77-9 C₂₉H₅₄O₂Si 
• 928-17-6 (R)-β-hydroxypalmitic acid 
• 185155-54-8 (R)-(-)-1-benzyloxy-3-hexadecyl acetate 

Relevant academic research and scientific papers

An efficient and stereoselective route to 1-deoxy-5-hydroxy sphingosine analogues

A short and efficient synthesis of 1-deoxy-5-hydroxy sphingolipid is described. The key steps involved are a Jacobsen hydrolytic kinetic resolution (HKR) and Shibasaki's asymmetric Henry reaction.

Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid

Diol (R)-(+)-3 is prepared either from the hydroxyketone 2 by reduction with fermenting baker's yeast or by hydrolysis of the dioxolane (R)-(+)-1 which is available from dimethyl D-malate as starting material. (R)-(+)-3 could be converted stereoselectively into (R)-(+)-4. Reaction of (+)-4 with dodecylmagnesium bromide yielded the alcohol (S)-(-)-5 with >99% ee. Its acetylation gave (S)-(+)-6 and hydrogenolysis gave the primary alcohol (S)-(+)-7 which could be oxidized selectively to (S)-(+)-8 wih NaIO4/RuCl3. Alkaline hydrolysis of (+)-8 yielded 3-hydroxyhexadecanoic acid (S)-(+)-9 which could be esterified to give the methyl ester (S)-(+)-10 with >99% ee. Starting with the dioxolane (S)-(-)-1, derived from dimethyl L-malate, the 3-hydroxyhexadecanoic acid (R)-(-)-10 could be synthesised via the intemediates (S)-(-)-3, (S)-(-)-4, (R)-(+)-5, (R)-(-)-6, (R)-(-)-7 and (R)-(-)-8. Copyright (C) Elsevier Science Ltd.