2'-CHLOROETHYL 2,3,4,6-TETRA-O-ACETYL-α-D-MANNOPYRANOSIDE - CAS 61198-76-3
Catalog number: 61198-76-3
Category: Main Product
Molecular Formula:
C16H23ClO10
Molecular Weight:
410.80082
COA:
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Purity:
95%
Synonyms:
2'-CHLOROETHYL 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSIDE
MSDS:
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1.2-Propynyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside.
Al-Mughaid H1, Robertson KN, Werner-Zwanziger U, Lumsden MD, Cameron TS, Grindley TB. Acta Crystallogr C. 2011 Feb;67(Pt 2):o60-3. doi: 10.1107/S010827011005225X. Epub 2011 Jan 7.
The 2-propynyl group in the title compound, C(17)H(22)O(10), adopts an exoanomeric conformation, with the acetylenic group gauche with respect to position C1. Comparison of (13)C NMR chemical shifts from solution and the solid state suggest that the acetylenic group also adopts a conformation anti to C1 in solution. The pyranose ring adopts a (4)C(1) conformation. Of the three secondary O-acetyl groups, that on position O4, flanked by two equatorial groups, adopts a syn conformation, in agreement with recent generalizations [González-Outeiriño, Nasser & Anderson (2005). J. Org. Chem. 70, 2486-2493]. The acetyl group on position O3 adopts a gauche conformation, also in agreement with the recent generalizations, but that on position O2 adopts a syn conformation, not in agreement with the recent generalizations.
2.Utilization of intrachain 4'-C-azidomethylthymidine for preparation of oligodeoxyribonucleotide conjugates by click chemistry in solution and on a solid support.
Kiviniemi A1, Virta P, Lönnberg H. Bioconjug Chem. 2008 Aug;19(8):1726-34. doi: 10.1021/bc800221p. Epub 2008 Aug 1.
4'-C-Azidomethylthymidine 3'-(H-phosphonate) monomer (10) was synthesized in high yield and three such monomers were incorporated by the H-phosphonate coupling into a 15-mer oligodeoxyribonucleotide. The unmodified 2'-deoxynucleosides could be coupled by either the H-phosphonate or phosphoramidite chemistry, indicating that the Staudinger reaction between the azido group and the phosphoramidite reagent severely hampered the coupling only when it took place intramolecularly. After chain assembly, three alkynyl group bearing ligands, viz., propargyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (2), N-{4-[N-(trifluoroacetyl)aminomethyl]benzyl}-4-pentynamide (3) and N (1), N (3), N (2')-tris(trifluoroacetyl)-N (6')-(4-pentynoyl)neamine (4), were conjugated to the azido groups of the oligonucleotide by click chemistry both on a solid support and in solution. The products were deprotected by conventional ammonolysis and purified by HPLC chromatography.
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CAS 61198-76-3 2'-CHLOROETHYL 2,3,4,6-TETRA-O-ACETYL-α-D-MANNOPYRANOSIDE

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