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【结 构 式】 
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【分子编号】16048 【品名】(1S)-1-[2-([(4aR,6R,7R,8R,8aR)-6-(benzyloxy)-2,2-dimethyl-8-[(9-phenylnonanoyl)oxy]hexahydropyrano[3,2-d][1,3]dioxin-7-yl]amino)-2-oxoethyl]dodecyl 9-phenylnonanoate 【CA登记号】 |
【 分 子 式 】C60H89NO9 【 分 子 量 】968.368 【元素组成】C 74.42% H 9.26% N 1.45% O 14.87% |
合成路线1
该中间体在本合成路线中的序号：(XI)2) The acylation of the amine group of benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside (IX) with 3(S)-hydroxytetradecanoic acid (II) by means of pivaloyl chloride in THF gives the corresponding amide (X), which is acylated with 9-phenylnonanoic acid (IV), 2-chloro-1-methylpyridinium iodide (CMPI) and dimethylaminopyridine to yield the fully esterified compound (XI). Elimination of the isopropylidene group of (XI) with acetic acid/water affords the dihydroxy compound (XII), which is treated with tert-butyldimethylsilyl chloride and DMAP to give (XIII) with the primary OH-group protected with a TBDMS group. Elimination of the benzyl protecting group of (XIII) by hydrogenation as before gives 2-deoxy-6-O-(tert-butyldimethylsilyl)-3-O-(9-phenylnonanoyl)-2-[3(S)-(9-phenylnonanoyloxy)tetradecanamido]-D-glucopyranose (XIV), which is sulfonated with SO3/pyridine complex in pyridine yielding the 4-O-sulfonated compound (XV). Finally, this compound is desilylated by means of acetic acid in methanol.
| 【1】 Toda, M.; Shimoji, K.; Sasaki, Y. (Ono Pharmaceutical Co., Ltd.); Novel glucopyranose derivs. EP 0226381; JP 1988179885 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 16039 | (3S)-3-hydroxytetradecanoic acid | 1961-72-4 | C14H28O3 | 详情 | 详情 |
| (IV) | 16041 | 9-phenylnonanoic acid | C15H22O2 | 详情 | 详情 | |
| (IX) | 16046 | (4aR,6R,7R,8R,8aS)-7-amino-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-ol | C16H23NO5 | 详情 | 详情 | |
| (X) | 16047 | (3S)-N-[(4aR,6R,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3-hydroxytetradecanamide | C30H49NO7 | 详情 | 详情 | |
| (XI) | 16048 | (1S)-1-[2-([(4aR,6R,7R,8R,8aR)-6-(benzyloxy)-2,2-dimethyl-8-[(9-phenylnonanoyl)oxy]hexahydropyrano[3,2-d][1,3]dioxin-7-yl]amino)-2-oxoethyl]dodecyl 9-phenylnonanoate | C60H89NO9 | 详情 | 详情 | |
| (XII) | 16049 | (2R,3R,4R,5R,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-3-([(3S)-3-[(9-phenylnonanoyl)oxy]tetradecanoyl]amino)tetrahydro-2H-pyran-4-yl 9-phenylnonanoate | C57H85NO9 | 详情 | 详情 | |
| (XIII) | 16050 | (2R,3R,4R,5R,6R)-2-(benzyloxy)-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-5-hydroxy-3-([(3S)-3-[(9-phenylnonanoyl)oxy]tetradecanoyl]amino)tetrahydro-2H-pyran-4-yl 9-phenylnonanoate | C63H99NO9Si | 详情 | 详情 | |
| (XIV) | 16044 | (2R,3R,4R,5R)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3,6-dihydroxy-5-([(3S)-3-[(9-phenylnonanoyl)oxy]tetradecanoyl]amino)tetrahydro-2H-pyran-4-yl 9-phenylnonanoate | C56H93NO9Si | 详情 | 详情 | |
| (XV) | 16052 | 6-O-(Tert-butyldimethylsilyl)-2-deoxy-3-O-(9-phenylnonanoyl)-2-[3(S)-(9-phenylnonanoyloxy)tetradecanamido]-4-O-sulfo-D-glucopyranose sodium salt | C56H92NNaO12SSi | 详情 | 详情 |