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【结 构 式】 
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【分子编号】60149 【品名】(2S,3R,4R,5R)-4,5-bis[(4-methoxybenzyl)oxy]-2-(propylsulfanyl)tetrahydro-2H-pyran-3-ol 【CA登记号】 |
【 分 子 式 】C24H32O6S 【 分 子 量 】448.58048 【元素组成】C 64.26% H 7.19% O 21.4% S 7.15% |
合成路线1
该中间体在本合成路线中的序号：(XV)D-xylose trichloroacetimidate intermediate (XVIII): The reaction of tetraacetyl-D-xylose (IX) with HBr/AcOH n dichloromethane gives the glycosyl bromide (X), which is treated with Et-SH and lutidine in nitromethane to yield the thio orthoester (XI). The deacetylation of (XI) by means of NaOMe in methanol affords dihydroxy compound (XII), whose OH groups are protected by means of Pmb-Cl and NaH to provide the bis 4-methoxybenzyl ether compound (XIII). ZnCl2 promoted ring opening of the thio orthoester group of (XIII) leads to the thioglycoside (XIV), which is deacetylated by means of NaOMe in methanol to give compound (XV). The acylation of the free OH group of (XV) with 4-methoxybenzoyl chloride (XVI), TEA and DMAP in dichloromethane yields the benzoate ester (XVII), which is finally converted into the target D-xylose trichloroacetimidate (XVIII) by reaction with NBS, Cl3C-CN and DBU in dichloromethane
| 【1】 Yu, W.; Jin, Z.; Total synthesis of the anticancer natural product OSW-1. J Am Chem Soc 2002, 124, 23, 6576. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 48936 | D-Arabinose tetraacetate | C13H18O9 | 详情 | 详情 | |
| (X) | 23761 | (2R,3R,4S,5R)-3,5-bis(acetoxy)-2-bromotetrahydro-2H-pyran-4-yl acetate | C11H15BrO7 | 详情 | 详情 | |
| (XI) | 60144 | (2S,3aR,6R,7S,7aR)-6-(acetyloxy)-2-methyl-2-(propylsulfanyl)tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-7-yl acetate | C14H22O7S | 详情 | 详情 | |
| (XII) | 60145 | (2S,3aR,6R,7S,7aR)-2-methyl-2-(propylsulfanyl)tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6,7-diol | C10H18O5S | 详情 | 详情 | |
| (XIII) | 60146 | (2S,3aR,6R,7S,7aR)-6,7-bis[(4-methoxybenzyl)oxy]-2-methyl-2-(propylsulfanyl)tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran; (2S,3aR,6R,7S,7aR)-6-[(4-methoxybenzyl)oxy]-2-methyl-2-(propylsulfanyl)tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-7-yl 4-methoxybenzyl ether | C26H34O7S | 详情 | 详情 | |
| (XIV) | 60147 | (2S,3R,4S,5R)-4,5-bis[(4-methoxybenzyl)oxy]-2-(propylsulfanyl)tetrahydro-2H-pyran-3-yl acetate | C26H34O7S | 详情 | 详情 | |
| (XV) | 60149 | (2S,3R,4R,5R)-4,5-bis[(4-methoxybenzyl)oxy]-2-(propylsulfanyl)tetrahydro-2H-pyran-3-ol | C24H32O6S | 详情 | 详情 | |
| (XVI) | 60148 | 4-methoxybenzoic acid | C8H8O3 | 详情 | 详情 | |
| (XVII) | 60150 | (2S,3R,4S,5R)-4,5-bis[(4-methoxybenzyl)oxy]-2-(propylsulfanyl)tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C32H38O8S | 详情 | 详情 | |
| (XVIII) | 48950 | (3R,4S,5R)-4,5-bis[(4-methoxybenzyl)oxy]-2-[(2,2,2-trichloroethanimidoyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C31H32Cl3NO9 | 详情 | 详情 |