|
【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% |
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 |