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ps331883028金蟲 (正式寫手)
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[求助]
急求幫忙翻譯三段摘要,化學(xué)類的,非常感謝。!急求!。
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The key intermediates in this synthesis are the protected glycosyl-isatines 7 and 8 which were prepared in four steps from the corresponding glycosyl-indolines 1 and 2, respectively.The preparation of compound 7 has been previously detailed[2].Glycosyl-indolines 1 and 2 were prepared by glycosylation of the corresponding indolines. The hydroxy groups of the sugar moiety were first acetylated before aromatization with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) and oxidation with chromium oxide to give the glycosylisatines 7 and 8 (Scheme 2). As mentioned in our previous paper for the synthesis of 1-(2,3,4,6-tetra-O-acetyl-b- D-glucopyranosyl)-5-nitroindolin-2,3-dione [2], the synthesis was more difficult in the presence of electron acceptor substituents. Indeed, the glycosylation step was achieved in 24 h for compound 1 and required 6 days for nitro analogue 2. The aromatization step was carried out at room temperature for 12 h for compound 5 and at 100 C for 3 days for nitro compound 6. At last, the oxidation with chromium oxide was performed and it resulted in 88% yield for compound 7 and only 46% yield for the 6-nitro analogue 8. The required diversely substituted indolin-2-one derivatives were either commercially available (5 and 6-chlorooxindole) or prepared by standard methods (Scheme 3). |

金蟲 (正式寫手)

木蟲 (小有名氣)
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在這個合成中關(guān)鍵的中間體是受保護(hù)的糖基靛紅7和8,這些分別都是從糖基靛紅1和2通過四步反應(yīng)制備的;衔7的制備之前已經(jīng)詳細(xì)講述。糖基靛紅1和2是通過相應(yīng)的二氫吲哚糖基化得到的。糖的烴基有一部分在DDQ芳構(gòu)化之前首先被乙;,用氧化鉻氧化得到糖基靛紅7和8。(方案2) 因?yàn)橹耙呀?jīng)提到1-(2,3,4,6-四面體-0-乙;-b-吡喃葡萄糖基)-5-硝基吲哚-2,3-二酮,在有受體存在的情況下合成更難發(fā)生。糖基化步驟需要反應(yīng)24小時(shí)得到化合物1,并且需要6天得到硝基類似物2.芳構(gòu)化步驟需在室溫下反應(yīng)12小時(shí)得到化合物5,并且在100℃3天得到硝基化合物6.最后再用氧化鉻進(jìn)行氧化,得到化合物7的產(chǎn)率是88%,而6-硝基類似物8只有46%的收率。 所需的不同的代替物吲哚-2-one派生物是市場上可以買到的(5,6-氯代烴吲哚)或者通過標(biāo)準(zhǔn)方法制備。(方案3) 有些專業(yè)詞可能不太準(zhǔn)確,僅供參考! |

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受保護(hù)的糖基-靛紅素7和8是這個合成中的關(guān)鍵中間體,它們分別由相應(yīng)的糖基-吲哚1和2通過四步反應(yīng)制備而成;衔7的制備之前已經(jīng)詳細(xì)介紹過[2]。糖基-吲哚1和2是由相應(yīng)的吲哚糖基化后制備而成的。糖的一部分羥基基團(tuán)在2,3-二氯-5,6-二氰-對苯醌 (DDQ)芳構(gòu)化和氧化鉻氧化之前首先被乙酰化,這樣得到糖基靛紅7和8。(方案2) 在我們先前文章中提到的合成1-(2,3,4,6-四面體-O-乙;-b-D-吡喃葡萄糖基)-5-硝基吲哚-2,3二酮[2],在有電子受體取代基存在的情況下合成更難發(fā)生。事實(shí)上,糖基化步驟進(jìn)行24小時(shí)得到化合物1,得到硝基類似物2需要進(jìn)行6天。芳構(gòu)化步驟在室溫下反應(yīng)12小時(shí)得到化合物5,在100℃反應(yīng)3天得到硝基化合物6。最后,氧化鉻的氧化反應(yīng)得到化合物7的產(chǎn)率是88%,而6-硝基類似物8的產(chǎn)率只有46%。 所需的不同的替代吲哚-2-酮的衍生品都是市場上可以買到的(5和6-氯氧化吲哚)或標(biāo)準(zhǔn)方法可以制備的(方案3)。 |
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