185155-49-1

Basic information

• Product Name: 3-Hexadecanol, 1-(phenylmethoxy)-, (S)-
• CAS NO: 185155-49-1
• Molecular Formula: C23H40O2
• Molecular Weight: 348.569
• Mol File: 185155-49-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Hexadecanol, 1-(phenylmethoxy)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hexadecanol, 1-(phenylmethoxy)-, (S)-(185155-49-1)
• EPA Substance Registry System: 3-Hexadecanol, 1-(phenylmethoxy)-, (S)-(185155-49-1)

Safety Data

• Hazardous Substances Data: 185155-49-1(Hazardous Substances Data)

Upstream product

• 115114-87-9 (2R)-2-(2-benzyloxyethyl)oxirane 
• 143-15-7 1-dodecylbromide 
• 6278-91-7 4-(benzyloxy)-2-butanone 
• 185155-56-0 4-benzyloxy-1-bromo-butan-2-one 
• 185155-48-0 4-benzyloxy-1-hydroxybutan-2-one 
• 100-44-7 benzyl chloride 
• 159517-86-9 (R)-(+)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 69985-32-6 (R)-4-phenylmethoxy-1,2-butanediol 

Downstream Products

• 51883-36-4 (R)-β-hydroxyhexadecanoic acid methyl ester 
• 185155-50-4 (S)-(+)-1-benzyloxy-3-hexadecyl acetate 

Relevant articles and documents

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.