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【结 构 式】 
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【分子编号】37869 【品名】 【CA登记号】 |
【 分 子 式 】C41H41ClF6N4O13S 【 分 子 量 】979.3048192 【元素组成】C 50.29% H 4.22% Cl 3.62% F 11.64% N 5.72% O 21.24% S 3.27% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The compound was obtained by solid-phase synthesis on an aminoethyl-photolinker AM resin. Deprotection of hydroxyl and amino groups from disaccharide-resin (I) by means of hydrazine provided (II). Reaction of the resulting free C-2' amino group of (II) with 3-(trifluoromethyl)benzoic acid (III) in the presence of HATU afforded the corresponding amide (IV). Reacetylation of (IV) with acetic anhydride and dimethylaminopyridine gave triacetate (V). Subsequent reduction of the azido group of (V) by means of trimethyl phosphine provided the C-3 amine (VI), which was condensed with 4-chloro-3-(trifluoromethyl)phenyl isocyanate (VII) yielding urea (VIII).
| 【1】 Allanson, N.; Sofia, M.J.; Hatzenbuhler, N.T.; et al.; Discovery of novel disaccharide antibacterial agents using a combinatorial library approach. J Med Chem 1999, 42, 17, 3193. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 37863 | (2R,3R,4R,5R,6S)-3-(acetoxy)-2-[(acetoxy)methyl]-6-[[(2S,3R,4S,5S,6S)-6-(aminocarbonyl)-4-azido-5-methoxy-2-(phenylsulfanyl)tetrahydro-2H-pyran-3-yl]oxy]-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)tetrahydro-2H-pyran-4-yl acetate | C33H35N5O13S | 详情 | 详情 | |
| (II) | 37864 | (2S,3S,4S,5R,6S)-5-[[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]-4-azido-3-methoxy-6-(phenylsulfanyl)tetrahydro-2H-pyran-2-carboxamide | C19H27N5O8S | 详情 | 详情 | |
| (III) | 17890 | 3-(trifluoromethyl)benzoic acid; m-Trifluoromethylbenzoic acid | 454-92-2 | C8H5F3O2 | 详情 | 详情 |
| (IV) | 37865 | (2S,3S,4S,5R,6S)-4-azido-5-[((2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[[3-(trifluoromethyl)benzoyl]amino]tetrahydro-2H-pyran-2-yl)oxy]-3-methoxy-6-(phenylsulfanyl)tetrahydro-2H-pyran-2-carboxamide | C27H30F3N5O9S | 详情 | 详情 | |
| (V) | 37866 | (2R,3R,4R,5R,6S)-3-(acetoxy)-2-[(acetoxy)methyl]-6-[[(2S,3R,4S,5S,6S)-6-(aminocarbonyl)-4-azido-5-methoxy-2-(phenylsulfanyl)tetrahydro-2H-pyran-3-yl]oxy]-5-[[3-(trifluoromethyl)benzoyl]amino]tetrahydro-2H-pyran-4-yl acetate | C33H36F3N5O12S | 详情 | 详情 | |
| (VI) | 37867 | (2R,3R,4R,5R,6S)-3-(acetoxy)-2-[(acetoxy)methyl]-6-[[(2S,3R,4S,5S,6S)-4-amino-6-(aminocarbonyl)-5-methoxy-2-(phenylsulfanyl)tetrahydro-2H-pyran-3-yl]oxy]-5-[[3-(trifluoromethyl)benzoyl]amino]tetrahydro-2H-pyran-4-yl acetate | C33H38F3N3O12S | 详情 | 详情 | |
| (VII) | 37868 | 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene; 4-chloro-3-(trifluoromethyl)phenyl isocyanate | 327-78-6 | C8H3ClF3NO | 详情 | 详情 |
| (VIII) | 37869 | C41H41ClF6N4O13S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VIII)Cleavage of the anomeric thiophenyl group of (VIII) by means of mercuric trifluoroacetate produced the desired lactol (IX). Attachment of the phospholipid unit to lactol (IX) was carried out by reaction with phosphoramidite (X). The resulting phosphite ester (XI) was then oxidized to phosphate (XII) using meta-chloroperbenzoic acid. Subsequent basic hydrolysis of (XII) removed the protecting groups to give (XIII). Finally, photolytic cleavage of the resin (XIII) furnished the title disaccharide derivative.
| 【1】 Allanson, N.; Sofia, M.J.; Hatzenbuhler, N.T.; et al.; Discovery of novel disaccharide antibacterial agents using a combinatorial library approach. J Med Chem 1999, 42, 17, 3193. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 37869 | C41H41ClF6N4O13S | 详情 | 详情 | ||
| (IX) | 37870 | C35H37ClF6N4O14 | 详情 | 详情 | ||
| (X) | 37871 | methyl 2-[[(2-cyanoethyl)(diisopropylamino)phosphino]oxy]hexadecanoate | C26H51N2O3P | 详情 | 详情 | |
| (XI) | 37872 | C55H73ClF6N5O18P | 详情 | 详情 | ||
| (XII) | 37873 | C55H73ClF6N5O19P | 详情 | 详情 | ||
| (XIII) | 37874 | C45H62ClF6N4O16P | 详情 | 详情 |