三芳香基醚類之官能化去保謢及引進新官能基反應的探討

徐蕾蕾(Lei-Lei Hsu)

指導教授 ： 陳建添

國立臺灣師範大學/理學院/化學系/碩士(1999年)

摘要

無資料

關鍵字

三芳香基甲基醚 ； 官能化去保護 ； 葡萄醣 ； 固相合成技術 ； 寡醣的連結合成

並列摘要

Abstract
We prepared different types of triarylmethyl chlorides based on xanthene. They can transform into triarylmethyl ethers with 2-phenylethanol and 3-phenyl-1-propanol. These substrates can be functionally deprotected with various electrophiles, include unsaturated aliphatic, aromatic acyl chloride, triflate, sulfonyl chloride, phosphonyl chloride and silyl chlorides. Out of 5 different solvents investigated, dichloromethane and acetonitrile were found to be the best solvents leading to the highest yield and fast reaction. We have also developed a new type of triarylmethyl chlorides based on xanthene. We have successful transform triarylmethyl ether to relative esters, ethers, phosphonates and alkyl silyl ethers derivatives. More important, acyl chloride derivatives can be deprotected with concomitant introdution of nitro-, bromo-, methyl chloro- and ethylene. These derivatives may be further converted to other functions, nitro- compound reduce to amine group, and it can be transformed into diazonium salts or another functional groups. Methoxy group can proceed SN2 reaction with alkyl halide after deprotection of methoxy group. Besides, the bromo group can be introduced into the aromatic ring by coupling reaction. The resultant triarylmethyl ethers can be deprotected with concomitant introduction of a new functional groups such as esters, alkyl (silyl) ethers, sulfonates, and phosphonates. The last two derivatives may be further converted into azides and iodides. According to the initial results the synthetic methods are potentially applicable to hydrocarbon chemistry. Acorrding to the above results, we prepared the carbohydrates systems base on (D)-glucose and triarylmethyl chloride under pyridine. We can get compound 88 and it can treated with p-vinylbenzoyl chloride to get compound 89. Componud 89 have already successful used on the synthesis of oligosaccrides.

並列關鍵字

trityl ether ； functionally deprotected ； (D)-glucose ； solid state synthesis ； the synthesis of oligosaccrides

參考文獻

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