【结 构 式】 |
【分子编号】47674 【品名】N-([(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-methylpyrrolidinyl]methyl)acetamide 【CA登记号】 |
【 分 子 式 】C30H36N2O4 【 分 子 量 】488.62692 【元素组成】C 73.74% H 7.43% N 5.73% O 13.1% |
合成路线1
该中间体在本合成路线中的序号:(XXII)The reduction of aldehyde (XV) with DIBAL in dichloromethane gives the carbinol (XVI), which is treated with Ms-Cl and TEA to yield the mesylate (XVII). The reaction of (XVII) with sodium azide in DMF affords the corresponding azide (XVIII), which is reduced with H2 over Pd/C in methanol to provide the amino compound (XIX). The reaction of (XIX) with Ac2O in pyridine gives the expected amide (XX), which is treated with TFA to eliminate the carbamate protecting group, thus yielding pyrrolidine (XXI). The reductive methylation of (XXI) with formaldehyde and NaBH3CN in methanol affords the N-methylated pyrrolidine (XXII), which is finally deprotected by hydrogenation with H2 over Pd/C in methanol.
【1】 Takebayashi, M.; Kajimoto, T.; Kanie, O.; Hiranuma, S.; Kanie, Y.; Wong, C.-H.; A versatile synthetic strategy for the preparation and discovery of new iminocyclitols as inhibitors of glucosidases. J Org Chem 1999, 64, 14, 5280. |
【2】 Wong, C.-H.; Liu, J. (Scripps Research Institute); Iminocyclitol inhibitors of hexoaminidase and glycosidase. WO 0068194 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(XV) | 47667 | tert-butyl (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-formyl-1-pyrrolidinecarboxylate | C32H37NO6 | 详情 | 详情 | |
(XVI) | 47668 | tert-butyl (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-(hydroxymethyl)-1-pyrrolidinecarboxylate | C32H39NO6 | 详情 | 详情 | |
(XVII) | 47669 | tert-butyl (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-[[(methylsulfonyl)oxy]methyl]-1-pyrrolidinecarboxylate | C33H41NO8S | 详情 | 详情 | |
(XVIII) | 47670 | tert-butyl (2R,3R,4R,5R)-2-(azidomethyl)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-pyrrolidinecarboxylate | C32H38N4O5 | 详情 | 详情 | |
(XIX) | 47671 | tert-butyl (2R,3R,4R,5R)-2-(aminomethyl)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-pyrrolidinecarboxylate | C32H40N2O5 | 详情 | 详情 | |
(XX) | 47672 | tert-butyl (2R,3R,4R,5R)-2-[(acetamido)methyl]-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-pyrrolidinecarboxylate | C34H42N2O6 | 详情 | 详情 | |
(XXI) | 47673 | N-([(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]pyrrolidinyl]methyl)acetamide | C29H34N2O4 | 详情 | 详情 | |
(XXII) | 47674 | N-([(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-methylpyrrolidinyl]methyl)acetamide | C30H36N2O4 | 详情 | 详情 |