With the rapid development of chemical substances, we look forward to future research findings about 55357-38-5.
The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 55357-38-5, name is 2-Hydroxy-N,N,N-trimethylethanaminium 4-methylbenzenesulfonate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Hydroxy-N,N,N-trimethylethanaminium 4-methylbenzenesulfonate
Fig. 2. Synthesis of the novel phospholipid analogs 1-O-DPPC and 1-O-DPPG’ with the phosphate in the C-2 position from (S)-O-benzyl glycidol. (a) C16H33OH,NaH, DMF/THF (71%); (b) i. POCl3, Et3N, DCM, ii. Pyridine, Choline tosylate EPO (65%); (c) H2, Pd/C, MeOH (99%); (d) C15H31COOH, DMAP, Et3N, DCM (83%); (e) (1-Pr)2NP(OMe)Cl, TMP, DCM; (f) i. (R)-isopropylidene glycerol, Phenyl- IH- tetrazole, DCM, ii. t-BuOOH (67% over 2 steps); (g) H2, Pd/C, MeOH (99%); (h) Palmitic acid, DMAP, DCC, DCM (92%); (i) i. CH3CN, isopropanol, Me3N, DCM, ii. HCl, MeOH, DCM, H2O, iii. NaHCO3, DCM (70%).; The unnatural PC and PG phospholipids (1-O-DPPC, 1-O-DPPG’) with the phos- phocholine and phosphoglycerol head groups linked to the C-2 position of the glyc¬ erol moiety were synthesized utilizing (S)-O-benzyl glycidol as a versatile starting material [27,28] as shown in Fig. 2. Opening of the epoxide 1 under basic condi¬ tions, using THF/DMF (1:1) as a solvent system that minimizes dimerization gave 2 in 71% yield after purification by column chromatography. The phosphorylation was performed using phosphorous oxychloride in CH2Cl2 [27], which gave 3 in 65% yield. Debenzylation under H2 atmosphere with Pd/C as catalyst followed by a sim¬ ple acylation using palmitoyl chloride gave the target 1-O-DPPC lipid. The synthe¬ sis of 1-O-DPPG’ was carried out from 2 using (1-Pr)2NPClOMe [31] as the phos- phorylation reagent. The phosphorylation using TMP as base in the lipid coupling followed by (R)-isopropylidene glycerol with 5-phenyl-lH-tetrazole as a weak pro¬ ton donor gave the protected phospholipid 4 in 67% yield after oxidation. Debenzy¬ lation followed by acylation using DCC gave 5 in 92% yield. Deprotection of lipid 5 was carried out with Me3N to remove the methyl protection group, followed by stir- ring in CH2Cl2/MeOH/0.5M HCl (65:25:4) resulting in removal of the isopro- pylidene group. Finally, the proton on the phosphate was exchanged with sodium us- EPO ing NaHCO3, which gave the desired 1-O-DPPG’ in 70% yield after purification by column chromatography. AEL-43 and AEL-44 were obtained by simple deprotec- tion. Debenzylation of 3 under H2 with Pd/C as catalyst gave AEL-43 in quantitative yield. Deprotection of 4 was carried out using Me3N, CH2Cl2/MeOH/0.5M HCl (65:25:4) as described above followed by debenzylation using H2-PdZC which gave AEL-44 in 71% yield.
With the rapid development of chemical substances, we look forward to future research findings about 55357-38-5.
Reference:
Patent; LIPLASOME PHARMA A/S; WO2006/48017; (2006); A1;,
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