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【结 构 式】

【分子编号】56342

【品名】N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-4-[(E)-2-butenyloxy]-6-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-3-yl]acetamide

【CA登记号】

【 分 子 式 】C24H35NO7

【 分 子 量 】449.54444

【元素组成】C 64.12% H 7.85% N 3.12% O 24.91%

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:(XXIV)

In an alternative route, 2-N-acetyl-4,6-O-isopropylidene-D-glucosamine benzyl pyranoside (XVII) was alkylated with 1-bromo-2-butene (XVIII) in the presence of barium oxide and barium hydroxide to produce the 3-O-crotyl ether (XIX). After acidic hydrolysis of the isopropylidene ketal (XIX), the resultant diol (XX) was selectively mono-acylated at the primary hydroxyl with benzoyl chloride (XXI) to afford the 6-benzoate ester (XXII). Protection of the 3-hydroxyl group of (XXII) by means of dihydropyran (DHP) and p-toluenesulfonic acid gave rise to the tetrahydropyranyl ether (XXIII). After methanolysis of the benzoate ester of (XXIII) in the presence of NaOMe, the resultant primary alcohol (XXIV) was protected as the benzyl ether (XXV). Subsequent hydrolysis of the tetrahydropyranyl group of (XXV) in aqueous HOAc furnished the protected glucosamine intermediate (XXVI).

1 Kiso, M.; et al.; A general, convenient synthesis of the repeating, disaccharide-dipeptide unit of the bacterial, cell-wall peptidoglycan by the oxazoline method. Carbohydr Res 1980, 83, 1, C8.
2 Kiso, M.; et al.; Synthesis and immunoadjuvant activities of the repeating, disaccharide-dipeptide unit of the bacterial, cell-wall peptidoglycan and of some carbohydrate analogs. Carbohydr Res 1982, 104, 2, 253.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVII) 56337 N-[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide C18H25NO6 详情 详情
(XVIII) 35252 (E)-1-bromo-2-butene 29576-14-5 C4H7Br 详情 详情
(XIX) 56338 N-{(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-[(E)-2-butenyloxy]-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl}acetamide C22H31NO6 详情 详情
(XX) 56339 N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-4-[(E)-2-butenyloxy]-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]acetamide C19H27NO6 详情 详情
(XXI) 10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
(XXII) 56340 {(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-4-[(E)-2-butenyloxy]-3-hydroxytetrahydro-2H-pyran-2-yl}methyl benzoate C26H31NO7 详情 详情
(XXIII) 56341 [(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-4-[(E)-2-butenyloxy]-3-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yl]methyl benzoate C31H39NO8 详情 详情
(XXIV) 56342 N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-4-[(E)-2-butenyloxy]-6-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-3-yl]acetamide C24H35NO7 详情 详情
(XXV) 56343 N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-6-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]-5-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-3-yl]acetamide C31H41NO7 详情 详情
(XXVI) 56344 N-{(2S,3R,4R,5S,6R)-2-(benzyloxy)-6-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]-5-hydroxytetrahydro-2H-pyran-3-yl}acetamide C26H33NO6 详情 详情
Extended Information