本研究的目的在合成出帶有胺基的單醣、雙醣、三醣、四醣類化合物和多種羧酸進行耦合後，在未純化的狀態下將其加入不同種類的癌細胞株中進行毒性檢測。
合成帶有胺基的化合物分別為Gal-O-(CH2)3CH2N3、雙醣Gal(1→6)Gal、三醣 及四醣 。予體(2R,3S,4S,5R,6S)-2-(azidomethyl)-6-((trichloromethylamino)methoxy)
tetrahydro-2H-pyran-3,4,5-triyl tribenzoate和乳糖及半乳糖所合成的受體進行醣基化反應，得到(2R,3S,4S,5R,6S)-2-(((2S,3R,4S,5S,6R)-6-
(azidomethyl)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yloxy)methyl)-6-((2R,3R,4S,5R,6S)-4,5-bis(benzoyloxy)-2-(benzoyloxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3-yloxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (70%)及(2R,3S,4S,5R,6S)-2-(((2S,3R,4S,5S,6R)-6
-(azidomethyl)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yloxy)methyl)-6-((2R,3R,4S,5R,6S)-2-(((2S,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yloxy)methyl)-4,5-bis(benzoyloxy)-6-(p-tolylthio)tetrahydro-2H-pyran-3-yloxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (63%)產物，在三醣的反應中α構型和β構型的比例約為1/9。另一方面，過程中觀察到由於空間的障礙使得Phenyl O-(2,6-Di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-( 1-4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside及(2S,3R,4S,5R,6R)-4-
acetoxy-5-((2S,3R,4S,5R,6R)-3-(benzoyloxy)-6-(benzoyloxymethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yloxy)-6-(benzoyloxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3-yl benzoate的C-3、C-3’和C-4’二級氫氧基團的活性降低。
2-(azidomethyl)-6-((trichloromethylamino)methoxy)tetrahydro
-2H-pyran-3,4,5-triyl tribenzoate經過八步合成總產率5%。衍生出的linker (4-azidobutan-1-ol)經過氫化之後，就可以成為核心合物((2R,3R,4S,5R,6R)-2-(4-aminobutoxy)-6-(aminomethyl)tetrahydro-2H-pyran-3,4,5-triol)，便可在分子庫的建立及生物分析上使用。

The aim of this research is to generate the monosaccharide, disaccharide, trisaccharide and tetrasaccharide of galactose bearing amine groups which would be used for coupling with numerous carboxylic acids. The coupled products in the mixture was directly submitted to a screen assay for their cytotoxicities against the cancer cell lines.

Monosaccharide Gal-O-(CH2)3CH2N3, disaccharide Gal(1→6)Gal, trisaccharide and tetrasaccharide have been successfully prepared. Glycosylation of the 2-(azidomethyl)-6-
((trichloromethylamino)methoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate, bearing the active leaving group of imidate, with the acceptors of galactose and lactose derivative to provide (2R,3S,4S,5R,6S)-2-(((2S,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yloxy)methyl)-6-((2R,3R,4S,5R,6S)-4,5-bis(benzoyloxy)-2-(benzoyloxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3-yloxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate and (2R,3S,4S,5R,6S)-
2-(((2S,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yloxy)methyl)-6-((2R,3R,4S,5R,6S)-2-(((2S,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yloxy)methyl)-4,5-bis(benzoyloxy)-6-(p-tolylthio)tetrahydro-2H-pyran-3-yloxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate in 70% and 63% yield, respectively. The ratio of α-form and β-form of the trisaccharide was α/β=1/9. On the other hand, a poor yield of the glycosylation of 2-(azidomethyl)-6-
((trichloromethylamino)methoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate, Phenyl O-(2,6-Di-O-benzoyl-3,4-O-isopropylidene-β-D-
galactopyranosyl)-( 1-4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside and (2S,3R,4S,5R,6R)-4-acetoxy-5-((2S,3R,4S,5R,6R)-3-(benzoyloxy)-
6-(benzoyloxymethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yloxy)-6-(benzoyloxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3-yl benzoate was observed. This could be accounted for the steric hindrance of the second alcohol at C-3, C-3’ and C-4’ of Phenyl O-(2,6-Di-O-benzoyl-
3,4-O-isopropylidene-β-D-galactopyranosyl)-( 1-4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside and (2S,3R,4S,5R,6R)-4-acetoxy-5-
((2S,3R,4S,5R,6R)-3-(benzoyloxy)-6-(benzoyloxymethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yloxy)-6-(benzoyloxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3-yl benzoate.
2-(azidomethyl)-6-((trichloromethylamino)methoxy)tetrahydro
-2H-pyran-3,4,5-triyl tribenzoate can be prepared via a 8 step synthesis in total 5% yield. The extended linker with azide group of 4-azidobutan-1-ol after hydrogenation could provide the desired core amine, (2R,3R,4S,5R,6R)-2-(4-aminobutoxy)-6-(aminomethyl)tetrahydro-2H-pyran-3,4,5-triol. It will be submitted to the library construction and the corresponding bioassay.

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