Synthesis and properties of 35S, 14C and 3H labeled S-alkyl glycerol ethers and derivatives

✍ Scribed by William J. Ferrell; Antonio Garces; Etienne A. Desmyter

• Publisher: Elsevier Science
• Year: 1976
• Tongue: English
• Weight: 413 KB
• Volume: 16
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(76)90022-0

✦ Synopsis

P, adioactive S-alkyl glycerol ethers have been synlhesized with 3SS, 14C and 3tt labels as well as 311/35S double labels. Tile synthesized compounds were converted to various derivatives which can serve to characterize tile S-alkyl glycerol ethers. These included tile isopropylidene derivative, oxidation with periodate to the aldehyde followed by reduction with LiAIH4 to tile alcohol, and reaction of tile alcohol with acetic anhydride to form tile acetate derivative.

Chemical analysis, IR, NMR, zonal TLC profile scans and GLC showed all the products to be "-,997( pure.

Tile GLC behavior of the aldehyde and acetate derivatives of both S-alkyl glycerol ethers and O-alkyl glycerol ethers on EGSS-X was compared. C H3(CHz)nCHzOH ~ CH~EHz)I1CHzBr C H3(CHz)nCHzSH CHIS H m n fH,O" > CHI-S-C HI'(C H~ ~IC H-~ ~H,OH ,v CH,OH /j CHaOH IC H~-S-CHz(CHl)nCH~l C H~-S-CHI(CH,~C H , H/C~o v, HC--O~ /CH~ l ~.C\ i HzO-O / CH 3 V CHE'S-CHz(CH,),CH , CHi-S-CH~12H~)nCH, HzCO H • HzC-O-~CH3 0 VII VIII