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【结 构 式】 
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【分子编号】54316 【品名】ethyl 2-(2'-methoxy[1,1'-biphenyl]-3-yl)acetate 【CA登记号】n/a |
【 分 子 式 】C17H18O3 【 分 子 量 】270.32812 【元素组成】C 75.53% H 6.71% O 17.76% |
合成路线1
该中间体在本合成路线中的序号：(I)The Friedel-Crafts condensation of 2-(2'-methoxybiphenyl-3-yl)acetic acid ethyl ester (I) with adipoyl dichloride (II) by means of AlCl3 gives the adduct (III), which is treated with BBr3 to cleave the methoxy groups and yield the diphenolic compound (IV). The condensation of (IV) with alpha-D-mannose pentaacetate (V) by means of BF3/Et2O affords the bis glycoside (VI), which is hydrolyzed with aq. LiOH aq. or NaOH to provide the dicarboxylic acid (VII). Finally, both ketonic groups of (VII) are reduced with LiOH and N2H4, or with Et3SiH, TFA and BF3/Et2O, or with H2, Pd(OH)2 and BBr3, to furnish the target bis mannopyranoside.
| 【1】 Dupré, B.; Beck, P.J.; Vanderslice, P.; Hu, X.; Scott, I.L.; Kassir, J.M.; McAbee, K.L.; Bui, H.; Dixon, R.A.F.; Kogan, T.P.; Novel synthetic inhibitors of selectin-mediated cell adhesion: Synthesis of 1, 6-bis[3-(3-carboxymethylphenyl)-4-(2-alpha-D-mannopyranosyloxy)phenyl]hexane (TBC1269). J Med Chem 1998, 41, 7, 1099. |
| 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) | 54316 | ethyl 2-(2'-methoxy[1,1'-biphenyl]-3-yl)acetate | n/a | C17H18O3 | 详情 | 详情 |
| (II) | 52933 | Hexanedioyl dichloride; Adipoyl chloride | C6H8Cl2O2 | 详情 | 详情 | |
| (III) | 54317 | ethyl 2-(5'-{6-[3'-(2-ethoxy-2-oxoethyl)-6-methoxy[1,1'-biphenyl]-3-yl]-6-oxohexanoyl}-2'-methoxy[1,1'-biphenyl]-3-yl)acetate | n/a | C40H42O8 | 详情 | 详情 |
| (IV) | 54318 | ethyl 2-(5'-{6-[3'-(2-ethoxy-2-oxoethyl)-6-hydroxy[1,1'-biphenyl]-3-yl]-6-oxohexanoyl}-2'-hydroxy[1,1'-biphenyl]-3-yl)acetate | n/a | C38H38O8 | 详情 | 详情 |
| (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 |
| (VI) | 54320 | ethyl 2-[5'-{6-[3'-(2-ethoxy-2-oxoethyl)-6-({(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)[1,1'-biphenyl]-3-yl]-6-oxohexanoyl}-2'-({(3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)[1,1'-biphenyl]-3-yl]acetate | n/a | C66H74O26 | 详情 | 详情 |
| (VII) | 54321 | 2-(5'-[6-(3'-(2-hydroxy-2-oxoethyl)-6-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}[1,1'-biphenyl]-3-yl)-6-oxohexanoyl]-2'-{[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}[1,1'-biphenyl]-3-yl)acetic acid | n/a | C46H50O18 | 详情 | 详情 |