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【结 构 式】 
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【分子编号】27256 【品名】(2R,3R,4R,5R,6S)-5-[[(2S)-2-(acetamido)-3-methyl-3-sulfanylbutanoyl]amino]-4,6-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-2H-pyran-3-yl acetate 【CA登记号】 |
【 分 子 式 】C21H32N2O11S 【 分 子 量 】520.55796 【元素组成】C 48.45% H 6.2% N 5.38% O 33.81% S 6.16% |
合成路线1
该中间体在本合成路线中的序号：(VII)Condensation of glucosamine (I) with anisaldehyde (II) gave imine (III). Subsequent acetylation of (III) with Ac2O in pyridine produced the tetra O-acetate (IV). The imine group of (IV) was then hydrolyzed with HCl in aqueous acetone to afford, after basic work-up, glucosamine tetraacetate (V), which was coupled with N-acetyl penicillamine using 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate to yield amide (VII). Finally, nitrosation of the mercapto group of (VII) with NaNO2 and HCl furnished the title compound.
| 【1】 Butler, A.R.; Megson, I.L.; Greig, I.R. (University of St. Andrews); Nitric oxide donor drugs. WO 9820015 . |
| 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) | 24036 | (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol; Glucosamine | 3416-24-8 | C6H13NO5 | 详情 | 详情 |
| (II) | 27251 | 4-methoxybenzaldehyde; Anisicaldehyde; p-anisaldehyde | 123-11-5 | C8H8O2 | 详情 | 详情 |
| (III) | 27252 | (3R,4R,5S,6R)-6-(hydroxymethyl)-3-[[(E)-(4-methoxyphenyl)methylidene]amino]tetrahydro-2H-pyran-2,4,5-triol | C14H19NO6 | 详情 | 详情 | |
| (IV) | 27253 | (2R,3R,4R,5R,6S)-4,6-bis(acetoxy)-2-[(acetoxy)methyl]-5-[[(E)-(4-methoxyphenyl)methylidene]amino]tetrahydro-2H-pyran-3-yl acetate | C22H27NO10 | 详情 | 详情 | |
| (V) | 27254 | (2R,3R,4R,5R,6S)-4,6-bis(acetoxy)-2-[(acetoxy)methyl]-5-aminotetrahydro-2H-pyran-3-yl acetate | C14H21NO9 | 详情 | 详情 | |
| (VI) | 27255 | (2S)-2-(acetamido)-3-methyl-3-sulfanylbutyric acid | 59-53-0 | C7H13NO3S | 详情 | 详情 |
| (VII) | 27256 | (2R,3R,4R,5R,6S)-5-[[(2S)-2-(acetamido)-3-methyl-3-sulfanylbutanoyl]amino]-4,6-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-2H-pyran-3-yl acetate | C21H32N2O11S | 详情 | 详情 |