127875-22-3Relevant academic research and scientific papers
A NOVEL PROCEDURE FOR THE PREPARATION OF 1-OH SUGAR DERIVATIVES USING 2-METHOXYETHYL GLYCOSIDES
Morishima, Naohiko,Koto, Shinkiti,Kanemitsu, Kumi,Zen, Shonosuke
, p. 1189 - 1190 (1983)
Treatment of benzyl-protected 2-methoxyethyl glycopyranosides with titanium tetrachloride followed by hydrolysis provides a new method for the preparation of the corresponding 1-OH sugar derivatives.The present method is shown to be useful for the prepara
Total synthesis of the: Helicobacter pylori serotype O2 O-antigen α-(1 → 2)- And α-(1 → 3)-linked oligoglucosides
Tian, Guangzong,Qin, Chunjun,Liu, Zhonghua,Shen, Dacheng,Zou, Xiaopeng,Fu, Junjie,Hu, Jing,Seeberger, Peter H.,Yin, Jian
supporting information, p. 344 - 347 (2020/01/13)
Exploiting synergistic remote participation effects of acyl groups at the O3 and O6 positions was key to the complete α-selectivity during the total synthesis of the unique (1 → 2)- and (1 → 3)-linked α-oligoglucosides from the Helicobacter pylori O2 O-antigen. Acyl remote participation and solvent effects were found to counteract during α-stereoselective glucosylations for the first time. The resulting antigen is a lead for the development of a carbohydrate-conjugate vaccine.
Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound
-
, (2019/06/07)
The invention discloses discloses synthesis of a helicobacter-pylorus O2 serotype O antigen oligosaccharide compound, and belongs to the field of organic synthesis. According to the synthesis, helicobacter-pylorus O2 serotype O-antigen disaccharide to tet
Is an acyl group at O-3 in glucosyl donors able to control α-stereoselectivity of glycosylation? the role of conformational mobility and the protecting group at O-6
Komarova, Bozhena S.,Orekhova, Maria V.,Tsvetkov, Yury E.,Nifantiev, Nikolay E.
, p. 70 - 76 (2014/04/03)
The stereodirecting effect of a 3-O-acetyl protecting group, which is potentially capable of the remote anchimeric participation, and other protecting groups in 2-O-benzyl glucosyl donors with flexible and rigid conformations has been investigated. To this aim, an array of N-phenyltrifluoroacetimidoyl and sulfoxide donors bearing either 3-O-acetyl or 3-O-benzyl groups in combination with 4,6-di-O-benzyl, 6-O-acyl-4-O-benzyl, or 4,6-O-benzylidene protecting groups was prepared. The conformationally flexible 3-O-acetylated glucosyl donor protected at other positions with O-benzyl groups demonstrated very low or no α-stereoselectivity upon glycosylation of primary or secondary acceptors. On the contrary, 3,6-di-O-acylated glucosyl donors proved to be highly α-stereoselective as well as the donor having a single potentially participating acetyl group at O-6. The 3,6-di-O-acylated donor was shown to be the best α-glucosylating block for the primary acceptor, whereas the best α-selectivity of glycosylation of the secondary acceptor was achieved with the 6-O-acylated donor. Glycosylation of the secondary acceptor with the conformationally constrained 3-O-acetyl-4,6-O-benzylidene-protected donor displayed under standard conditions (-35 C) even lower α-selectivity as compared to the 3-O-benzyl analogue. However, increasing the reaction temperature essentially raised the α-stereoselectivities of glycosylation with both 3-O-acetyl and 3-O-benzyl donors and made them almost equal. The stereodirecting effects of protecting groups observed for N- phenyltrifluoroacetimidoyl donors were also generally proven for sulfoxide donors.2013 Elsevier Ltd. All rights reserved.
