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【结 构 式】 
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【分子编号】11997 【品名】1-[(3aR,4R,6R,6aR)-6-(Hydroxymethyl)-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,4(1H,3H)-pyrimidinedione 【CA登记号】 |
【 分 子 式 】C11H14N2O7 【 分 子 量 】286.24144 【元素组成】C 46.16% H 4.93% N 9.79% O 39.13% |
合成路线1
该中间体在本合成路线中的序号：(II)A new synthesis of 2',3'-dideoxyadenosine has been described: The reaction of uridine (I) with methyl orthoformate and p-toluenesulfonic acid gives the cyclic orthoester (II), which is acetylated with acetic anhydride at 100 C to the acetate (III). The reaction of (III) with acetic anhydride at temperatures over 120 C yields 5'-O-acetyl-2',3'-dideoxy-2',3'-didehydrouridine (IV), which is hydrogenated to 5'-O-acetyl-2',3'-dideoxyuridine (V).
| 【1】 Shiragami, H.; Shirae, H.; Irie, Y.; Yokozeki, K.; Yasuda, N.; The synthesis of 2',3'-dideoxyadenosine and 2',3'-dideoxyinosine. Nucl Acid Res Symp Ser 1988, 20, 20, 17-18. |
| 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) | 11996 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; Uridine | 58-96-8 | C9H12N2O6 | 详情 | 详情 |
| (I) | 12001 | 1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | 5983-09-5 | C9H12N2O4 | 详情 | 详情 |
| (II) | 11997 | 1-[(3aR,4R,6R,6aR)-6-(Hydroxymethyl)-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,4(1H,3H)-pyrimidinedione | C11H14N2O7 | 详情 | 详情 | |
| (III) | 11998 | [(3aR,4R,6R,6aR)-6-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate | C13H16N2O8 | 详情 | 详情 | |
| (IV) | 11999 | [(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl acetate | C11H12N2O5 | 详情 | 详情 | |
| (V) | 12000 | [(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl acetate | C11H14N2O5 | 详情 | 详情 | |
| (VI) | 12001 | 1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | 5983-09-5 | C9H12N2O4 | 详情 | 详情 |
| (VII) | 10343 | 9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine | 73-24-5 | C5H5N5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)2) The reaction of uridine (I) with methyl orthoformate and p-toluenesulfonic acid gives the cyclic orthoester (II), which is acetylated with acetic anhydride at 100 C, yielding the 5'-acetoxy derivative (III). The reaction of (III) with acetic anhydride at temperatures over 120 C affords 5'-O-acetyl-2',3'-dideoxy-2',3'-didehydrouridine (IV), which is hydrogenated to 5'-O-acetyl-2',3'-dideoxyuridine (V). Hydrolysis of (V) affords 2',3'-dideoxyuridine (VI), which is finally submitted to a transdideoxyribosylation with hypoxanthine (VII) by incubation in an appropriate medium with Escherichia coli AJ 2595 resting cells.
| 【1】 Shiragami, H.; Shirae, H.; Irie, Y.; Yokozeki, K.; Yasuda, N.; The synthesis of 2',3'-dideoxyadenosine and 2',3'-dideoxyinosine. Nucl Acid Res Symp Ser 1988, 20, 20, 17-18. |
| 【2】 Shirae, H.; Kobayashi, K.; Shiragami, H.; Irie, Y.; Yasuda, N.; Yokozeki, K.; Production of 2',3'-dideoxyadenosine and 2',3'-dideoxyinosine from 2',3'-dideoxyuridine and the corresponding purine bases by resting cells of Escherichia coli AJ 2595. Appl Environ Microbiol 1989, 55, 2, 419-24. |
| 【3】 Prous, J.; Castaner, J.; DIDEOXYINOSINE. Drugs Fut 1990, 15, 6, 569. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 60593 | p-xylene | C8H10 | 详情 | 详情 | ||
| (I) | 11996 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; Uridine | 58-96-8 | C9H12N2O6 | 详情 | 详情 |
| (II) | 11997 | 1-[(3aR,4R,6R,6aR)-6-(Hydroxymethyl)-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,4(1H,3H)-pyrimidinedione | C11H14N2O7 | 详情 | 详情 | |
| (III) | 11998 | [(3aR,4R,6R,6aR)-6-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2-methoxytetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate | C13H16N2O8 | 详情 | 详情 | |
| (IV) | 11999 | [(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl acetate | C11H12N2O5 | 详情 | 详情 | |
| (V) | 12000 | [(2S,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl acetate | C11H14N2O5 | 详情 | 详情 | |
| (VI) | 12001 | 1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | 5983-09-5 | C9H12N2O4 | 详情 | 详情 |
| (VII) | 12794 | 9H-Purin-6-ol; Hypoxanthine | 68-94-0 | C5H4N4O | 详情 | 详情 |