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【结 构 式】 
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【分子编号】46984 【品名】(2S,3S,4S,6R)-4-iodo-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl acetate 【CA登记号】 |
【 分 子 式 】C9H15IO4 【 分 子 量 】314.12017 【元素组成】C 34.41% H 4.81% I 40.4% O 20.37% |
合成路线1
该中间体在本合成路线中的序号：(IV)Reduction of ketone (I) with NaBH4 in MeOH at low temperature yielded alcohol (II) as the major product. This was treated with trifluoromethanesulfonic anhydride to provide triflate (III), which was displaced with NaI to form iodide (IV). Acetolysis of the methyl pyranoside (IV) produced the 1-alpha-O-acetyl derivative (V) along with minor amounts of the beta-anomer. The reaction of (V) with dry HCl in benzene gave the corresponding glycosyl chloride, which was subsequently coupled with daunorubicinone (VI) using HgO and HgBr2 to provide the title compound as the major anomer.
| 【1】 Pierre, A.; Aligiannis, N.; Skaltsounis, A.-L.; Marakos, P.; Leonce, S.; Atassi, G.; Pouli, N.; Mitaku, S.; Design, synthesis and biological activity of 7-O-(4-O-acetyl-3-iodo-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)daunomycinone and 7-O-(3-chloro-2,3,6-trideoxy-4-O-propanoyl-alpha-L-lyxo-hexopyranosyl)daunomycinone. Chem Pharm Bull 2000, 48, 1, 150. |
| 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) | 46981 | (2S,3S,6R)-6-methoxy-2-methyl-4-oxotetrahydro-2H-pyran-3-yl acetate | C9H14O5 | 详情 | 详情 | |
| (II) | 46982 | (2S,3R,4R,6R)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl acetate | C9H16O5 | 详情 | 详情 | |
| (III) | 46983 | (2S,3S,4R,6R)-6-methoxy-2-methyl-4-[[(trifluoromethyl)sulfonyl]oxy]tetrahydro-2H-pyran-3-yl acetate | C10H15F3O7S | 详情 | 详情 | |
| (IV) | 46984 | (2S,3S,4S,6R)-4-iodo-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl acetate | C9H15IO4 | 详情 | 详情 | |
| (V) | 46985 | (2S,3S,4S,6S)-6-(acetoxy)-4-iodo-2-methyltetrahydro-2H-pyran-3-yl acetate | C10H15IO5 | 详情 | 详情 | |
| (VI) | 16223 | (8S,10S)-8-acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione | 21794-55-8 | C21H18O8 | 详情 | 详情 |