96093-53-7

Upstream product

• 10550-58-0 (R)-3-(hexadecyloxy)-1,2-propanediol 
• 76-83-5 trityl chloride 
• 112-82-3 hexadecanyl bromide 
• 36653-82-4 1-Hexadecanol 
• 129940-50-7 (S)-tritylglycidol 
• 57959-37-2 3-O-hexadecyl-1,2-O-isopropylidene-sn-glycerol 
• 20779-14-0 methanesulfonic acid hexadecyl ester 

Downstream Products

• 98244-36-1 (S)-2-benzyloxy-1-hexadecyloxy-3-trityloxy-propane 
• 115406-33-2 1-O-hexadecyl-2-O-(3-isoxazolyl)-3-O-triphenylmethyl-sn-glycerol 
• 121358-36-9 4-Nitro-benzenesulfonic acid (S)-1-hexadecyloxymethyl-2-trityloxy-ethyl ester 
• 96022-71-8 2-O-Benzyl-3-O-hexadecyl-1-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-sn-glycerin 
• 1283128-67-5 N-((R)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl)formamide 
• 1283128-73-3 C₄₈H₆₂F₃NO₄ 
• 1283128-74-4 C₄₈H₆₂F₃NO₄ 
• 1283128-77-7 C₂₉H₄₈F₃NO₄ 
• 1283128-78-8 C₂₉H₄₈F₃NO₄ 
• 1263034-14-5 2-amino-2-deoxy-1-O-hexadecyl-3-O-trityl-sn-glycerol 
• 112014-14-9 1-Hexadecyl-2-(4-nitrobenzenesulfonyl)-D-glycerol 
• 96801-55-7 1-O-hexadecyl-2-deoxy-2-thio-S-acetyl-sn-glyceryl-3-phosphorylcholine 
• 112014-15-0 1-hexadecyl-2-thioacetyl-2-deoxyglycerol 
• 177167-83-8 1-O-hexadecyl-2-S-trityl-sn-2-thioglycero-3-O-phosphocholine 

Relevant academic research and scientific papers

Structure and synthesis of a unique isonitrile lipid isolated from the marine mollusk actinocyclus papillatus

The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the a

Methods employing and compositions containing defined oxidized phospholipids for prevention and treatment of atherosclerosis

Novel synthetic forms of etherified oxidized phospholipids and methods of utilizing same for preventing and treating atherosclerosis and other related disorders, as well as inflammatory disorders, immune mediated diseases, autoimmune diseases and proliferative disorders, are provided. In addition, methods of synthesizing etherified and esterified oxidized phospholipids and of using same for preventing and treating atherosclerosis and other related disorders are also provided.

A Stereoselective and Highly Practical Synthesis of Cytosolic Phospholipase A2 Substrate, 2-S-Arachidonoyl-1-O-hexadecyl-sn-2-thioglycero-3-O-phosphocholine

The substrate 1 of cytosolic phospholipase A2 (cPLA2) is an ether-type thiophospholipid with arachidonic acid at the C-2 position and is required for the chromogenic assay for reliable and convenient high throughput screening. The original method of synthesis of 1 has significant problems, resulting in extremely low overall yield and purity. We developed a novel and highly practical method of preparing sufficient quantities of pure 1 for assay. Our synthetic sequence is started with commercially available 1,2-O-isopropylidene-sn-grycerol (5) and is based on the following key steps: trityl migration reaction of 10 with boron trifluoride etherate to form 13, phosphocholine-forming reaction of 13 to yield 15, and efficient conversion of 15 into 1 by deprotection of a trityl group and condensation with arachidonic acid. Our method offers a practical means of large-scale production of 1 with excellent high chemical purity, because of the introduction of arachidonic acid at the last step of the synthetic sequence.

STEREOSPECIFIC SYNTHESIS OF PAF ANALOGUES. PREPARATION OF 1-HEXADECYL 2-THIOACETYL-2-DEOXYGLYCEROPHOSPHOCHOLINE (2-THIOPAF)

A new stereospecific synthesis of ether-phospholipids leading to 2-ThioPAF is reported.

Stereoselective Synthesis of Long-chain 1-O-(β-D-Maltosyl)-3-O-alkyl-sn-glycerols (Alkyl Glyceryl Ether Lysoglycolipids)

The synthesis of long-chain 2-O-benzyl-3-O-alkyl-sn-glycerols 5 was improved, making these compounds easily accessible for glycosylation experiments.Glycosylation with α-acetobromomaltose following a modified Koenings-Knorr procedure after removal of the protective groups yielded the title compound 9 in good yields.These compounds represent examples of alkyl glyceryl ether lysoglycolipids.Some properties of these amphiphilic compounds with a nonionic carbohydrate head-group differ not much (critical micell concentration, hemolytic activity), other properties differ very much (antitumor efficiency) from the properties of the analogous compounds with a zwitterionic phosphorylcholine head-group.