67227-89-8Relevant academic research and scientific papers
Oligosaccharide compound and its manufacture and its intermediate
-
, (2018/04/14)
The purpose of the present invention is to provide an oligosaccharide with high versatility that can produce a protected sulfate oligosaccharide that can become a manufacturing intermediate of polysulfated hyaluronic acid, and to provide a manufacturing method therefor and an intermediate thereof. Position 2 amino groups in glucosamine, galactosamine, and the like can react with saccharide receptors having an electron attracting group such as glucuronic acid and protected sulfate groups, by using a saccharide donor protected by a specific protective group.
Stereoselective synthesis of α-glycosyl azides by TMSOTf-mediated ring opening of 1,6-anhydro sugars
Lepage, Mathieu L.,Bodlenner, Anne,Compain, Philippe
, p. 1963 - 1972 (2013/05/21)
Access to α-glycosyl azides in modest to high diastereoselectivity by way of TMSN3 ring-opening of 1,6-anhydro sugars mediated by TMSOTf is reported. The reaction tolerates a wide variety of functional groups including alcohol, alkyne, azide and ester groups. The efficient synthesis of a pseudopentasaccharide in five steps from commercially available levoglucosan by way of a "click-click" approach is presented to highlight the interest of the TMSN3 ring-opening reaction. A new route to α-glycosyl azides by way of TMSN3 ring-opening of 1,6-anhydro sugars is presented. The potential of this methodology is demonstrated by the expeditious synthesis of a pseudopentasaccharide following a "click-click" approach.
Synthesis of a (1->6)-β-Linked N-Acetyl-D-glucosamine Oligosaccharide
Kanno, Ken-Ichi,Kobayashi, Yuichi,Nishimura, Shin-Ichiro,Kuzuhara, Hiroyoshi,Hatanaka, Kenichi
, p. 481 - 490 (2007/10/02)
1,6-Anhydro-2-deoxy-3,4-di-O-benzyl-2-phthalimido-β-D-glucopyranose (5) was synthesized from 1,6-anhydro-β-D-mannopyranose (1) in five steps.Compound 5 was polymerized under cationic conditions and selectively yielded glucosamine oligomers (degree of poly
Practical Synthesis of β-D-Xyl-(1->2)-β-D-Man-(1->4)-α-D-Glc-OMe, a Trisaccharide Component of the Hyriopsis schlegelii Glycosphingolipid
Lichtenthaler, Frieder W.,Schneider-Adams, Thomas,Immel, Stefan
, p. 6735 - 6738 (2007/10/02)
By employing the readily accessible (preceding paper in this issue) 3,4,6-tri-O-benzyl-α-D-arabino-hexosyl bromide (1) as an indirect, β-specific mannosyl donor, a practical three-step synthesis was elaborated for methyl xylosyl-β(1->2)-mannosyl-β(1->4)-g
Facile Preparation of 1,6-Anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose and Its 4-O-Substituted Derivatives
Sakairi, Nobuo,Takahashi, Shunya,Wang, Feng,Ueno, Yoshihito,Kuzuhara, Hiroyoshi
, p. 1756 - 1758 (2007/10/02)
Treatment of 1,6-anhydro-2,3-O-endo-benzylidene-β-D-mannopyranose derivatives with trimethylamine-borane (1/1)-aluminium chloride resulted in highly regioselective fission of the cyclic acetals to give the corresponding 2-O-unprotected-3-O-benzyl derivatives. Trifluoromethane-sulfonylation of these, followed by nucleophilic substitution, afforded 2-azido-2-deoxy derivatives in good yields.
A Mild Procedure for the Preparation of 1,6-Anhydro-β-D-hexopyranoses and Derivatives
Lafont, Dominique,Boullanger, Paul,Cadas, Olivier,Descotes, Gerard
, p. 191 - 194 (2007/10/02)
Treatment of reducing 6-O-tosyl-D-glucopyranoses 1 with 1,8-diazabicycloundec-7-ene (DBU) afforded the corresponding 1,6-anhydro-β-D-hexopyranoses 2 in high yields.Reaction was also performed on partly acetylated tosylates of carbohydrates.
Regioselective De-O-benzylation with Lewis Acids
Hori, Hiroshi,Nishida, Yoshihiro,Ohrui, Hiroshi,Meguro, Hiroshi
, p. 1346 - 1353 (2007/10/02)
Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.
Facile Preparation of 3,4-Di-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose and Some Derivatives Thereof: Useful Precursors for Oligosaccharide Synthesis
Dasgupta, Falguni,Garegg, Per J.
, p. 626 - 628 (2007/10/02)
A facile, virtually one-pot synthesis of the title compound and also some of its derivatives is based on regioselective 2-substitutions of 1,6-anhydro-β-D-mannopyranose using stannylidene activation.The compounds thus prepared are useful precursors in the synthesis of glycoprotein-type oligosaccharides.
A New, High Yield Synthesis of 2-Deoxy-2-fluoro-D-glucose
Haradahira, Terushi,Maeda, Minoru,Kai, Yasunobu,Kojima, Masaharu
, p. 364 - 365 (2007/10/02)
The reaction of 1,6-anhydro-3,4-di-O-benzyl-2-O-(trifluoromethanesulphonyl)-β-D-mannopyranose (4) with tetraalkylammonium fluorides provides a rapid, high yield synthetic route to 2-deoxy-2-fluoro-D-glucose.
Building Units of Oligosaccharides, XLVII. - Synthesis of Tri- and Tetrasaccharide Sequences of N-Glycoproteins Including a β-D-Mannosidic Linkage
Paulsen, Hans,Lebuhn, Rolf
, p. 1047 - 1072 (2007/10/02)
The trisaccharides α-D-Man-p-(1 -> 6)-β-D-Man-p-(1 -> 4)-D-GlcNAc (37) and α-D-Man-p-(1 -> 3)-β-D-Man-p-(1 -> 4)-D-GlcNAc (43) as well as the key tetrasaccharide α-D-Man-p-(1 -> 3)- 6)>-β-D-Man-p-(1 -> 4)-D-GlcNAc (51), which are parts of th
