1046465-35-3Relevant academic research and scientific papers
Mild Method for 2-Naphthylmethyl Ether Protecting Group Removal Using a Combination of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-Pinene
Lloyd, Dina,Bylsma, Marissa,Bright, Danielle K.,Chen, Xizhao,Bennett, Clay S.
, p. 3926 - 3934 (2017)
The use of a combination of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-pinene permits the removal of 2-naphthylmethyl (Nap) ether protecting groups on highly sensitive substrates. The reaction tolerates both acid and base sensitive protecting groups, and products are afforded in 68-96% yield. The utility of the method is demonstrated by the removal of the Nap protecting groups on highly sensitive 2,6-dideoxy-sugar disaccharides.
Synthesis of a tetrasaccharide phosphate from the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall
Lee, Yong Joo,Fulse, Dinanath Baburao,Kim, Kwan Soo
, p. 1574 - 1584 (2008/12/21)
The synthesis of dibenzyl 6-O-naphthylmethyl-2,3,5-tri-O-benzoyl-β-d-galactofuranosyl-(1→5)-2,3-di-O-benzoyl-6-O-benzyl-β-d-galactofuranosyl-(1→4)-3-O-benzyl-2-O-pivaloyl-α-l-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-4,6-di-O-benzoyl-α-d-glucopyranosyl phosphate (1), a protected form of the tetrasaccharide phosphate of the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall, has been accomplished. Key steps include the coupling of four monosaccharide building blocks with complete stereoselectivity by glycosylations employing thioglycosides, 2′-carboxybenzyl glycosides, and glycosyl fluorides as glycosyl donors. The α-glycosyl phosphate linkage was also stereoselectively elaborated by reaction of a tetrasaccharide hemiacetal with tetrabenzyl pyrophosphate in the presence of a base.
