【结 构 式】 |
【分子编号】41304 【品名】1-(3-chloropropoxy)-1-methylethyl methyl ether; 1-chloro-3-(1-methoxy-1-methylethoxy)propane 【CA登记号】 |
【 分 子 式 】C7H15ClO2 【 分 子 量 】166.6476 【元素组成】C 50.45% H 9.07% Cl 21.27% O 19.2% |
合成路线1
该中间体在本合成路线中的序号:(III)The reaction of 3-chloropropanol (I) with 2-methoxypropene (II) by means of PPTS gives the mixed ketal (III), which is condensed with diethyl malonate (IV) by means of sodium ethoxide in hot ethanol, affording the adduct (V). The reduction of (V) with NaH and Red-Al in refluxing toluene provides the allyl alcohol derivative (VI), which is submitted to an asymmetric epoxidation to give the epoxide (VII). The reaction of (VII) with octadecyl bromide (VIII) by means of NaH and tetrabutylammonium iodide (TBAI) yields the corresponding ether (IX), which by reaction with PPTS in HOAc is converted to the tetrahydrofuran-2-methanol derivative (X). Finally, this compound is condensed with POCl3, TEA, choline mesylate (XI) and DMAP in dichloromethane/pyridine to afford the target compound.
【1】 Lohmeyer, M.; Bittman, R.; Antitumor ether lipids and alkylphosphocholines. Drugs Fut 1994, 19, 11, 1021. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
41308 | 2-hydroxy-N,N,N-trimethyl-1-ethanaminium methanesulfonate | C6H17NO4S | 详情 | 详情 | ||
(I) | 19490 | 3-chloro-1-propanol | 627-30-5 | C3H7ClO | 详情 | 详情 |
(II) | 17354 | isopropenyl methyl ether; 2-methoxy-1-propene | 116-11-0 | C4H8O | 详情 | 详情 |
(III) | 41304 | 1-(3-chloropropoxy)-1-methylethyl methyl ether; 1-chloro-3-(1-methoxy-1-methylethoxy)propane | C7H15ClO2 | 详情 | 详情 | |
(IV) | 16829 | Diethyl malonate | 105-53-3 | C7H12O4 | 详情 | 详情 |
(V) | 41309 | diethyl 2-[3-(1-methoxy-1-methylethoxy)propyl]malonate | C14H26O6 | 详情 | 详情 | |
(VI) | 41305 | 2-[3-(1-methoxy-1-methylethoxy)propyl]-2-propen-1-ol | C10H20O3 | 详情 | 详情 | |
(VII) | 28797 | 1-bromooctadecane | 112-89-0 | C18H37Br | 详情 | 详情 |
(VIII) | 41306 | [(2S)-2-[3-(1-methoxy-1-methylethoxy)propyl]oxiranyl]methyl octadecyl ether; (2S)-2-[3-(1-methoxy-1-methylethoxy)propyl]-2-[(octadecyloxy)methyl]oxirane | C28H56O4 | 详情 | 详情 | |
(IX) | 41307 | [(2S)-2-[(octadecyloxy)methyl]tetrahydro-2-furanyl]methanol | C24H48O3 | 详情 | 详情 |