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【结 构 式】

【分子编号】18544

【品名】(3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

【CA登记号】

【 分 子 式 】C27H30O5

【 分 子 量 】434.5322

【元素组成】C 74.63% H 6.96% O 18.41%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

Condensation of protected fucopyranose (I) with Z-serine methyl ester (II) in the presence of trimethylsilyl triflate afforded fucosylated serine derivative (III). Then, selective elimination of benzyloxycarbonyl group was performed by hydrogenolysis in the presence of Pd/C to give amine (IV). Subsequent coupling with acid (V) using EDC and HOBt as the condensing reagents provided amide (VI). Hydrolysis of ester group of (VI) by treatment with LiI in pyridine gave acid (VII), which was condensed with glutamic acid derivative (VIII) to yield (IX). Finally, debenzylation of (IX) by hydrogenolysis in the presence of Pd(OH)2 provided the target compound.

1 Kiyoi, T.; Kondo, H.; A stereoselective alpha-fucosylation reaction using 1-hydroxy 2,3,4-tri-O-benzyl-L-fucose donor for the practical synthesis of selectin blocker. Bioorg Med Chem Lett 1998, 8, 20, 2845.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18544 (3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol C27H30O5 详情 详情
(II) 18545 methyl (2R)-2-[[(benzyloxy)carbonyl]amino]-3-hydroxypropanoate 1676-81-9 C12H15NO5 详情 详情
(III) 18546 methyl (2R)-2-[[(benzyloxy)carbonyl]amino]-3-[[(2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl]oxy]propanoate C39H43NO9 详情 详情
(IV) 18547 methyl (2R)-2-amino-3-[[(2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl]oxy]propanoate C31H37NO7 详情 详情
(V) 18548 2-tetradecylhexadecanoic acid C30H60O2 详情 详情
(VI) 18549 methyl (2R)-2-[(2-tetradecylhexadecanoyl)amino]-3-[[(2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl]oxy]propanoate C61H95NO8 详情 详情
(VII) 18550 (2R)-2-[(2-tetradecylhexadecanoyl)amino]-3-[[(2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl]oxy]propionic acid C60H93NO8 详情 详情
(VIII) 18551 benzyl (4S)-4-amino-5-(methylamino)-5-oxopentanoate C13H18N2O3 详情 详情
(IX) 18552 benzyl (4S)-5-(methylamino)-5-oxo-4-[((2R)-2-[(2-tetradecylhexadecanoyl)amino]-3-[[(2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl]oxy]propanoyl)amino]pentanoate C73H109N3O10 详情 详情
Extended Information