140397-45-1Relevant academic research and scientific papers
Synthesis of β-C-Glycopyranosyl Aldehydes and 2,6-Anhydro-heptitols
Khatri, Vinod,Kumar, Amit,Singh, Balram,Malhotra, Shashwat,Prasad, Ashok K.
, p. 11169 - 11174 (2015/11/18)
A convenient route has been developed for the diastereoselective synthesis of β-C-glycopyranosyl aldehydes from d-glucose, d-mannose, and d-galactose. The key step in the synthesis of C-glycosyl aldehydes is the aryl driven reductive dehydration on 1-phen
Preparation of 1-C-glycosyl aldehydes by reductive hydrolysis
Sipos, Szabolcs,Jablonkai, István
body text, p. 1503 - 1510 (2011/08/04)
Reductive hydrolysis of various protected glycosyl cyanides was carried out using DIBAL-H to form aldimine alane intermediates which were then hydrolyzed under mildly acidic condition to provide the corresponding aldehyde derivatives. While 1-C-formyl gly
Synthesis and conformational analysis of (α-D-Galactosyl) phenylmethane and α-,β-difluoromethane analogues: interactions with the plant lectin viscumin
Kolympadi, Maria,Fontanella, Marco,Venturi, Chiara,Andre, Sabine,Gabius, Hans-Joachim,Jimenez-Barbero, Jesus,Vogel, Pierre
scheme or table, p. 2861 - 2873 (2009/12/08)
(aα-D-Galactosyl)phenylmethane (1), (α- and β-D-galactosyl)-(difluoro)phenylmethane (2 and 3) have been prepared and their conformations in solution were described by using a combination of force-field calculations and NMR spectroscopic studies. Galactosi
New and general synthesis of β-C-glycosylformaldehydes from easily available β-C-glycosylpropanones
Norsikian, Stephanie,Zeitouni, Jennifer,Rat, Stephanie,Gerard, Sylvie,Lubineau, Andre
, p. 2716 - 2728 (2008/03/14)
A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation of β-C-d-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted doubl
Novel synthetic C-glycolipids, their synthesis and use to treat infections, cancer and autoimmune diseases
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, (2010/02/14)
The invention is directed to novel compounds of formulae (I), (II) and (III): wherein X is O or NH; R3 is OH or a monosaccharide and R4 is hydrogen, or R3 is hydrogen and R4 is OH or a monosaccharide; R5 is hydrogen or a monosaccharide; and pharmaceutically acceptable salts or esters thereof. The invention is also directed to the use of the compounds both directly and as immune adjuvants for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the intermediates which can be used to make these novel compounds.
A convenient new route to protected and free 2,6-anhydro-d-glycero-d-gulo- heptoses (1-formyl-β-D-glucopyranosides)
Zeitouni, Jennifer,Norsikian, Stéphanie,Lubineau, André
, p. 7761 - 7763 (2007/10/03)
A new and efficient process has been developed for the synthesis of 1-formyl-β-glucopyranosides from D-glucose.
Multigram scale synthesis of formyl tetra-O-benzyl-β-D-C-glucopyranoside using benzothiazole as a formyl group equivalent
Dondoni, Alessandro,Marra, Alberto
, p. 13 - 16 (2007/10/03)
The addition of 2-lithiobenzothiazole to D-gluconolactone followed by deoxygenation of the resulting ketose affords a mixture of benzothiazolyl α- and β-D-glucopyranoside; treatment of this mixture with sodium methoxide gives the β-anomer from which the title aldehyde is obtained in a pure form by transformation of the benzothiazole ring into the formyl group.
SYNTHETIC C-GLYCOLIPID AND ITS USE FOR TREATING CANCER INFECTIOUS DISEASES AND AUTOIMMUNE DISEASES
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Page 43; 47, (2010/02/06)
The invention is directed to compounds of formula (I) wherein X is O, OR NH; R' is a hydrocarbon chain; R and are hydrogen, OH or a monosaccharide; R is hydrogen or a monosaccharide; Q' is optionally present and may be a C1-10 hydrocarbon; X' i
An efficient diastereoselective synthesis of β-1-formyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside
Labéguère, Frédéric,Lavergne, Jean-Pierre,Martinez, Jean
, p. 7271 - 7272 (2007/10/03)
A diastereoselective synthesis of β-1-formyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside in four steps, using an umpolung Seebach reaction is described.
Synthesis of Novel Donor Mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as Potential Transferase Inhibitors
Schaefer, Andreas,Thiem, Joachim
, p. 24 - 29 (2007/10/03)
For the enzymatic transfer of galactose, N-acetylglucosamine, and N-acetylgalactosamine, UDP-Gal (1), UDP-GlcNAc (2), and UDP-GalNAc (3) are employed, and UDP serves as a feedback inhibitor. In this paper the synthesis of the novel UDP-sugar analogues 4, 5, and 6 as potential transferase inhibitors is described. Compounds 4-6 feature C-glycosidic hydroxymethylene linkages between the sugar and nucleoside moieties in contrast to the anomeric oxygens in the natural derivatives 1-3.
