83167-57-1

Upstream product

• 112-92-5 1-octadecanol 
• 14618-80-5 (R)-benzyl glycidol 
• 3386-32-1 n-octadecyl p-toluenesulfonate 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 638-66-4 n-Octadecanal 
• 10585-86-1 1,2-Di-O-isopropyliden-3-O-octadecyl-sn-glycerin 
• 16495-03-7 (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 83526-60-7 2-O-Acetyl-1-O-benzyl-3-O-octadecyl-sn-glycerin 
• 83526-52-7 3-O-Octadecyl-2-O-p-toluolsulfonyl-sn-glycerin 
• 83526-54-9 3-O-Octadecyl-1-O-p-toluolsulfonyl-sn-glycerin 
• 83537-01-3 (-)-1-O-octadecyl-2-O-acetyl-sn-glycerol 
• 83526-51-6 3-O-Octadecyl-2-O-p-toluolsulfonyl-3-O-trityl-sn-glycerin 
• 80707-96-6 Ro 15-4454 
• 83526-57-2 (S)-1-(benzyloxy)-3-(octadecyloxy)propan-2-ol 

Downstream Products

• 80459-30-9 2-O-Benzyl-1-O-octadecyl-3-O-trityl-sn-glycerin 
• 83526-55-0 (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol 
• 83526-75-4 (S)-1-O-octadecyl-3-acetylglycerol 
• 83526-72-1 3-O-Acetyl-1-O-octadecyl-sn-glycerin 
• 65492-82-2 (+)-Edelfosine 
• 80483-86-9 2-O-Benzyl-1-O-octadecyl-sn-glycero-3-phosphorylcholin 
• 80707-93-3 (S)-1-O-octadecyl-2-O-benzyl-glycerol 
• 74389-69-8 1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine 
• 83167-59-3 1-O-octadecyl-2-O-methyl-sn-glycerol 
• 38169-74-3 1-O-Octadecyl-3-O-trityl-sn-glycerin 
• 74430-89-0 Lyso-platelet-activating factor (C₁₈) 
• 83167-58-2 3-O-Benzyl-2-O-methyl-1-O-octadecyl-sn-glycerin 
• 83526-59-4 2-O-Acetyl-3-O-benzyl-1-O-octadecyl-sn-glycerin 
• 83537-02-4 3-O-Benzyl-2-O-formyl-1-O-octadecyl-sn-glycerin 

Relevant academic research and scientific papers

Stereoselective Synthesis of 1-O-Alkyl-3-O-benzyl-sn-glycerols and 1-O-Alkyl-2-O-methyl-3-O-β-D-glycosyl-sn-glycerols

Starting with D-mannitol, the yield of th synthesis of 3-O-benzyl-sn-glycerol (1) could be improved.The regioselective alkylation of 1 at the primary hydroxy group to the 1-O-alkyl-3-O-benzyl-sn-glycerols 3 was achieved by using the dibutylstannylene protecting group.The 1-O-alkyl-2-O-methyl-sn-glycerols 4, readily obtainable from 3, were successfully glycosylated under the conditions of the Koenigs-Knorr reaction to give 1-O-alkyl-2-O-methyl-3-O-β-D-glycosyl-sn-glycerols. - Key Words: Lysoglycolipids, glyceryl ethers / Stereoselective synthesis / Koenigs-Knorr reaction / Glyceryl ethers

Synthesis of Glycerophosphonolipids Containing Aminoalkylphosphonic Acids

1,2-Di-O-octadecyl- and 1,2-di-O-hexadecanoyl-sn-glycerol 3-(2-aminoethyl)phosphonate (21) and (22) and the (3-aminopropyl)phosphonate analogues (23) and (24) were prepared with the aim of obtaining enzyme (lipase)-stable liposomes.New reactions were devised and classic methodologies were modified in order to transform D-mannitol (6) into optically pure 1,2-di-O-substituted sn-glycerols (12) and (13) (R=C18H37 and C15H31CO).Benzyloxycarbonylaminoalkylphosphonic acids (5a) and (5b) were then coupled with the glycerols by means of condensing reagents such as 2,4,6-triisopropylbenzenesulphonyl chloride.The resulting N-protected lipids were catalitically hydrogenated to furnish compounds (21)-(24) in overall yields of 10-20 percent from compound (6).