110415-62-8Relevant articles and documents
SELECTIVE DEUTERATION OVER RANEY NICKEL IN DEUTERIUM OXIDE: METHYL GLYCOSIDES
Angyal, Stephen J.,Stevens, John D.,Odier, Leon
, p. 83 - 94 (1986)
The rate of protium-deuterium exchange, catalyzed by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied.In general, the exchange process is not highly regioselective in these compounds.However, conditions were found under which methyl β-D-fructopyranoside can be selectively labelled on C-5, methyl β-D-fructofuranoside on C-3, and methyl β-D-galactopyranoside on C-3 and C-4.
Synthesis and antiviral evaluation of nucleoside analogues bearing one pyrimidine moiety and two d-ribofuranosyl residues
Andreeva, Olga V.,Belenok, Mayya G.,Garifullin, Bulat F.,Kataev, Vladimir E.,Lyubina, Anna P.,Man’kova, Maria A.,Saifina, Liliya F.,Semenov, Vyacheslav E.,Shulaeva, Marina M.,Slita, Alexander V.,Volobueva, Alexandrina S.,Voloshina, Alexandra D.,Yesaulkova, Iana L.,Zarubaev, Vladimir V.
, (2021)
A series of 1,2,3-triazolyl nucleoside analogues in which 1,2,3-triazol-4-yl-β-D-ribofuranosyl fragments are attached via polymethylene linkers to both nitrogen atoms of the heterocycle moiety (uracil, 6-methyluracil, thymine, quinazoline-2,4-dione, alloxazine) or to the C-5 and N-3 atoms of the 6-methyluracil moiety was synthesized. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. Antiviral assays revealed three compounds, 2i, 5i, 11c, which showed moderate activity against influenza virus A H1N1 with IC50 values of 57.5 μM, 24.3 μM, and 29.2 μM, respectively. In the first two nucleoside analogues, 1,2,3-triazol-4-yl-β-D-ribofuranosyl fragments are attached via butylene linkers to N-1 and N-3 atoms of the heterocycle moiety (6-methyluracil and alloxazine, respectively). In nucleoside analogue 11c, two 1,2,3-triazol-4-yl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranose fragments are attached via propylene linkers to the C-5 and N-3 atoms of the 6-methyluracil moiety. Almost all synthesized 1,2,3-triazolyl nucleoside analogues showed no antiviral activity against the coxsackie B3 virus. Two exceptions are 1,2,3-triazolyl nucleoside analogs 2f and 5f, in which 1,2,3-triazol-4-yl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranose fragments are attached to the C-5 and N-3 atoms of the heterocycle moiety (6-methyluracil and alloxazine respectively). These compounds exhibited high antiviral potency against the coxsackie B3 virus with IC50 values of 12.4 and 11.3 μM, respectively, although both were inactive against influenza virus A H1N1. According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 2i, 5i, and 11c against the H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRp). As to the antiviral activity of nucleoside analogs 2f and 5f against coxsackievirus B3, it can be explained by their interaction with the coat proteins VP1 and VP2.
Selective monodeacetylation of methyl 2,3,5-tri-O-acetyl-D- arabinofuranoside using biocatalyst
Sook, Jin Jun,Man, Sik Moon,So, Ha Lee,Chan, Seong Cheong,Kwan, Soo Kim
, p. 5063 - 5065 (2005)
Methyl arabinofuranoside 1 was fully acetylated to methyl 2,3,5-tri-O-acetyl-d-arabinofuranoside 2 and it was regioselectively deacetylated using enzymes. Rhizopus oryzae esterase gave methyl 3,5-di-O-acetyl-d-arabinofuranoside 3, regioselectively. This protected 3 was deoxygenized to 3,5-di-O-acetyl-d-2-deoxyarabinofuranoside 7 using hypophosphorous acid.
Synthesis of the enantiomer of nelarabine
Herbal, Karim,Kitteringham, John,Voyle, Martyn,Whitehead, Andrew J.
, p. 2961 - 2964 (2005)
A synthesis of the enantiomer of nelarabine is described. Subtle changes in the protecting group strategy allow for an efficient inversion of the C-2′ stereocentre.
A stereoselective synthesis method for β-D-arabinofuran glycoside bonds
-
Paragraph 0043-0045; 0048, (2022/01/08)
The present invention belongs to the field of natural oligosaccharide chain synthesis technology, specifically relates to a β-D- arabinofuran glycoside bond stereoselective synthesis method, the present invention to 2- O- benzyl-3,5-O- xylene -D- arabfura
A Concise Synthesis of Oligosaccharides Derived From Lipoarabinomannan (LAM) with Glycosyl Donors Having a Nonparticipating Group at C2
Li, Zhihao,Zheng, Changping,Terreni, Marco,Bavaro, Teodora,Sollogoub, Matthieu,Zhang, Yongmin
supporting information, p. 2033 - 2044 (2020/03/04)
Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death over the world, and lipoarabinomannan (LAM) has been confirmed to play significant roles in this process. In this study, a convenient synthetic approach ha
