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【结 构 式】 
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【分子编号】54328 【品名】(2R,3S,4S,5S,6R)-3,5-bis[(2,2-dimethylpropanoyl)oxy]-2-{[(2,2-dimethylpropanoyl)oxy]methyl}-6-fluorotetrahydro-2H-pyran-4-yl pivalate 【CA登记号】n/a |
【 分 子 式 】C26H43FO9 【 分 子 量 】518.6204232 【元素组成】C 60.21% H 8.36% F 3.66% O 27.76% |
合成路线1
该中间体在本合成路线中的序号：(XIV)Treatment of alpha-D-mannose pentaacetate (V) with HF and pyridine in dichloromethane furnishes 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl fluoride (XIII), which is saponified with K2CO3 in MeOH and then submited to reesterification with pivaloyl chloride and DMAP in pyridine to yield the tetra-O-pivaloyl derivative (XIV). Mannosylation of compound (XV) with the pivaloyl protected compound (XIV) affords the bis glycoside derivative (XVI), which is finally converted into the desired product by first removal of the pivaloyl groups with NaOMe in MeOH/THF, followed by saponification of the ethyl ester groups with aqueous NaOH.
| 【1】 Scott, I.L.; et al.; Stereospecific alpha-D-mannosylation. Carbohydr Res 1999, 317, 1-4, 210. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 54319 | [(2R,3R,4S,5S,6R)-3,4,5,6-tetrakis(acetyloxy)tetrahydro-2H-pyran-2-yl]methyl acetate | n/a | C16H22O11 | 详情 | 详情 |
| (XIII) | 54329 | (2R,3S,4S,5S,6R)-3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-fluorotetrahydro-2H-pyran-4-yl acetate | n/a | C14H19FO9 | 详情 | 详情 |
| (XIV) | 54328 | (2R,3S,4S,5S,6R)-3,5-bis[(2,2-dimethylpropanoyl)oxy]-2-{[(2,2-dimethylpropanoyl)oxy]methyl}-6-fluorotetrahydro-2H-pyran-4-yl pivalate | n/a | C26H43FO9 | 详情 | 详情 |
| (XV) | 54327 | ethyl 2-(5'-{6-[3'-(2-ethoxy-2-oxoethyl)-6-hydroxy[1,1'-biphenyl]-3-yl]hexyl}-2'-hydroxy[1,1'-biphenyl]-3-yl)acetate | n/a | C38H42O6 | 详情 | 详情 |
| (XVI) | 54330 | (2R,3R,4S,5S)-3,5-bis[(2,2-dimethylpropanoyl)oxy]-2-{[(2,2-dimethylpropanoyl)oxy]methyl}-6-{[3'-(2-ethoxy-2-oxoethyl)-5-(6-{3'-(2-ethoxy-2-oxoethyl)-6-[((2R,3S,4S,5R,6R)-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]-6-{[(2,2-dimethylpropanoyl)oxy]methyl}tetrahydro-2H-pyran-2-yl)oxy][1,1'-biphenyl]-3-yl}-6-oxohexanoyl)[1,1'-biphenyl]-2-yl]oxy}tetrahydro-2H-pyran-4-yl 2,2-dimethylpropanoate | n/a | C90H122O26 | 详情 | 详情 |