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【结 构 式】 
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【分子编号】54326 【品名】2-[5'-{6-[3'-(2-hydroxy-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]hexyl}-2'-({(3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)[1,1'-biphenyl]-3-yl]acetic acid 【CA登记号】n/a |
【 分 子 式 】C62H70O24 【 分 子 量 】1199.2234 【元素组成】C 62.1% H 5.88% O 32.02% |
合成路线1
该中间体在本合成路线中的序号：(XII)The Friedel-Crafts condensation of 2-(2'-methoxybiphenyl-3-yl)acetic acid (VIII) with adipoyl dichloride (II) by means of AlCl3 in dichloromethane gives the adduct (IX), which is submitted to reduction of both carbonyl groups by means of LiOH and N2H4, or with Et3SiH, TFA and BF3/Et2O, or with H2, Pd(OH)2 and BBr3, to yield the hexane-1,6-diyl derivative (X). The cleavage of the methoxy groups of (X) by means of BBr3 in dichloromethane affords the bis phenolic compound (XI), which is condensed with alpha-D-mannose pentaacetate (V) by means of BF3/Et2O in dichloroethane to provide the bis glycoside (XII). Finally, this compound is hydrolyzed with LiOH in water to furnish the target bis mannopyranoside.
| 【1】 Mukherjee, A.K.; Dasgupta, F.; Novel synthetic inhibitors of selection-mediated cell adhesion: Synthesis of 1,6-bis [3-(3-carboxymethylphenyl)-4-(O-alpha-D-mannopyranosyl)phenyl]hexane (TBC 1269). Chemtracts - Org Chem 2000, 13, 9, 1431. |
| 【2】 Kogan, T.P.; Dupre, B.; Scott, I.L.; Bui, H.; Wheeler, K.L.; Keller, K.M.; Kassir, J.M. (Texas Biotechnology Corp.); Di- and trivalent small molecule selectin inhibitors. JP 1999508885; WO 9701335 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 52933 | Hexanedioyl dichloride; Adipoyl chloride | C6H8Cl2O2 | 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 |
| (VIII) | 54322 | 2-(2'-methoxy[1,1'-biphenyl]-3-yl)acetic acid | 187269-42-7 | C15H14O3 | 详情 | 详情 |
| (IX) | 54323 | 2-(5'-{6-[3'-(2-hydroxy-2-oxoethyl)-6-methoxy[1,1'-biphenyl]-3-yl]-6-oxohexanoyl}-2'-methoxy[1,1'-biphenyl]-3-yl)acetic acid | n/a | C36H34O8 | 详情 | 详情 |
| (X) | 54324 | 2-(5'-{6-[3'-(2-hydroxy-2-oxoethyl)-6-methoxy[1,1'-biphenyl]-3-yl]hexyl}-2'-methoxy[1,1'-biphenyl]-3-yl)acetic acid | n/a | C36H38O6 | 详情 | 详情 |
| (XI) | 54325 | 2-(2'-hydroxy-5'-{6-[6-hydroxy-3'-(2-hydroxy-2-oxoethyl)[1,1'-biphenyl]-3-yl]hexyl}[1,1'-biphenyl]-3-yl)acetic acid | n/a | C34H34O6 | 详情 | 详情 |
| (XII) | 54326 | 2-[5'-{6-[3'-(2-hydroxy-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]hexyl}-2'-({(3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)[1,1'-biphenyl]-3-yl]acetic acid | n/a | C62H70O24 | 详情 | 详情 |