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【结 构 式】

【分子编号】56348

【品名】N-[(4aR,6R,7R,8R,8aS)-6-({(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]tetrahydro-2H-pyran-3-yl}oxy)-8-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide

【CA登记号】

【 分 子 式 】C44H56N2O11

【 分 子 量 】788.93552

【元素组成】C 66.99% H 7.15% N 3.55% O 22.31%

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:(XXXI)

Glycosylation of the protected glucosamine (XXVI) with the glucopyranooxazoline (XXVII) was effected in the presence of p-toluenesulfonic acid in dichloroethane to give the protected chitobioside derivative (XXVIII). Methanolysis of the acetate esters of (XXVIII), followed by protection of the resultant triol (XXIX) with acetone dimethylacetal, gave rise to the 4',6'-isopropylidene derivative (XXX). The 3'-hydroxyl group of (XXX) was then protected as the benzyl ether (XXXI) with benzyl bromide in the presence of Ba(OH)2 and BaO. Removal of the 2-butenyl group of (XXXI) to furnish (XXXII) was performed by means of potassium tert-butoxide in hot DMSO. Subsequent alkylation of (XXXII) with (S)-2-chloropropionic acid (XI) led to acid (XXXIII).

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
(XI) 56332 (S)-(-)-2-Chloropropionic acid; (S)-2-Chloropropionic acid 29617-66-1 C3H5ClO2 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
(XXVII) 21969 (3aR,5R,6R,7R,7aR)-6-(acetoxy)-5-[(acetoxy)methyl]-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-7-yl acetate C14H19NO8 详情 详情
(XXVIII) 56345 (2R,3R,4R,5R,6R)-3-(acetylamino)-2-({(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]tetrahydro-2H-pyran-3-yl}oxy)-5-(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-4-yl acetate C40H52N2O14 详情 详情
(XXIX) 56346 N-[(2S,3R,4R,5S,6R)-2-({(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]tetrahydro-2H-pyran-3-yl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]acetamide C34H46N2O11 详情 详情
(XXX) 56347 N-[(4aR,6R,7R,8R,8aS)-6-({(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]tetrahydro-2H-pyran-3-yl}oxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide C37H50N2O11 详情 详情
(XXXI) 56348 N-[(4aR,6R,7R,8R,8aS)-6-({(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]-4-[(E)-2-butenyloxy]tetrahydro-2H-pyran-3-yl}oxy)-8-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide C44H56N2O11 详情 详情
(XXXII) 56349 N-[(4aR,6R,7R,8R,8aS)-6-({(2R,3S,4R,5R,6S)-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]-4-hydroxytetrahydro-2H-pyran-3-yl}oxy)-8-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide C40H50N2O11 详情 详情
(XXXIII) 56350 (2R)-2-({(2R,3S,4R,5R,6S)-3-{[(4aR,6R,7R,8R,8aS)-7-(acetylamino)-8-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-5-(acetylamino)-6-(benzyloxy)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran-4-yl}oxy)propanoic acid C43H54N2O13 详情 详情
Extended Information