(2R)-1-(benzyloxy)-3-(octadecyloxy)-2-propanol -Drug Synthesis Database

【结构式】

【分子编号】41263

【品名】(2R)-1-(benzyloxy)-3-(octadecyloxy)-2-propanol

【CA登记号】

【分子式】C₂₈H₅₀O₃

【分子量】434.7032

【元素组成】C 77.36% H 11.59% O 11.04%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

The reaction of (R)-O-benzylglycidol (I) with octadecanol (II) by means of NaH in hot DMF gives (R)-1-(benzyloxy)-3-(octadecyloxy)-2-propanol (III), which is methylated with methyl iodide and NaH in DMF yielding the corresponding methyl ether (IV). The debenzylation of (IV) with H2 over Pd/C in THF affords the primary alcohol (V), which is finally treated with POCl3/pyridine in CHCl3 and condensed with choline tosylate (VI) to furnish the target phosphorylcholine derivative.

参考文献中间体

合成目标

【1】 Bittman, R.; Lohmeyer, M.; Antitumor ether lipids and alkylphosphocholines. Drugs Fut 1994, 19, 11, 1021.
【2】 Barner, R.; Hirth, G.; Synthese von Glyceryätherphosphatiden. Herstellung von 1-O-octadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylchloline (`Platelet Activating Factor'), des Enantiomeren sowie einiger analoger Verbindungen. Helv Chim Acta 1982, 65, 1059-84.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12350	Benzyl (2R)oxiranylmethyl ether; (2R)-2-[(Benzyloxy)methyl]oxirane	14618-80-5	C₁₀H₁₂O₂	详情	详情
(II)	21494	1-octadecanol	112-92-5	C₁₈H₃₈O	详情	详情
(III)	41263	(2R)-1-(benzyloxy)-3-(octadecyloxy)-2-propanol		C₂₈H₅₀O₃	详情	详情
(IV)	41264	1-([[(2R)-2-methoxy-3-(octadecyloxy)propyl]oxy]methyl)benzene; benzyl (2R)-2-methoxy-3-(octadecyloxy)propyl ether		C₂₉H₅₂O₃	详情	详情
(V)	40717	(2S)-2-methoxy-3-(octadecyloxy)-1-propanol		C₂₂H₄₆O₃	详情	详情
(VI)	41265	2-hydroxy-N,N,N-trimethyl-1-ethanaminium 4-methylbenzenesulfonate		C₁₂H₂₁NO₄S	详情	详情

Extended Information