tert-butyl (2R,3R,4R,5R)-2-[(acetamido)methyl]-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】47672

【品名】tert-butyl (2R,3R,4R,5R)-2-[(acetamido)methyl]-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₃₄H₄₂N₂O₆

【分子量】574.71736

【元素组成】C 71.06% H 7.37% N 4.87% O 16.7%

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：(XX)

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.

参考文献中间体

合成目标

【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	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

Extended Information