18066-10-9Relevant academic research and scientific papers
Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal
Sang, Dayong,Yue, Huaxin,Zhao, Zhengdong,Yang, Pengtao,Tian, Juan
, p. 6429 - 6440 (2020/07/14)
Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.
Selective ether bond breaking method of aryl alkyl ether
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Paragraph 0238-0242, (2020/09/16)
The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.
Regioselective synthesis of 6-substituted 2-hydroxybenzaldehyde: Efficient synthesis of the immunomodulator tucaresol and related analogues
Zacharie, Boulos,Attardo, Giorgio,Barriault, Nancy,Penney, Christopher
, p. 2925 - 2929 (2007/10/03)
Two new improved procedures have been developed for the preparation of the immunostimulant tucaresol 1 [4-(2-formyl-3-hydroxyphenoxymethyl)benzoic acid]. These approaches, which start from resorcinol or 2,6-dimethoxybenzaldehyde, are practical and therefore amenable to scale-up. In the case of the second approach, the multi-step synthesis reported in the literature has been reduced to three steps. Furthermore, unlike the reported method, our synthesis is versatile for the preparation of tucaresol analogues. The method is general and applicable for the preparation of 6-substituted 2-hydroxybenzaldehydes.
Total synthesis of the gilvocarcins
Hosoya, Takamitsu,Takashiro, Eiji,Matsumoto, Takashi,Suzuki, Keisuke
, p. 1004 - 1015 (2007/10/02)
Convergent total syntheses of the aryl C-glycoside antibiotics gilvocarcin M (1a) and gilvocarcin V (1b) have been accomplished. Key steps include (1) contrasteric coupling of D-fucofuranosyl acetate 27 with iodophenol 26, which was achieved by employing
