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【结 构 式】 
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【分子编号】12242 【品名】5-Bromo-6-[((2R,3S)-3-[[tert-butyl(diphenyl)silyl]oxy]-5-methoxytetrahydro-2-furanyl)methoxy]-5-methyldihydro-2,4(1H,3H)-pyrimidinedione 【CA登记号】 |
【 分 子 式 】C27H35BrN2O6Si 【 分 子 量 】591.57428 【元素组成】C 54.82% H 5.96% Br 13.51% N 4.74% O 16.23% Si 4.75% |
合成路线1
该中间体在本合成路线中的序号：(III)A new synthesis of stavudine has been reported: The condensation of thymine (I) with methyl 2-deoxyribofuranoside (II) by means of N-bromosuccinimide (NBS) followed by protection with TBDPS-Cl gives the intermediate (III), which is cyclized by means of trimethylsilyl triflate (TMS-OTf), yielding the cyclothymidine derivative (IV). The deprotection of (IV) with tetrabutylammonium fluoride affords the unprotected compound (V), which is finally treated successively with triflate anhydride, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and Zn/acetic acid. The unprotected intermediate compound (V) can also be obtained by cyclization of thymidine (VI) by means of NBS in DMF, catalyzed by trifluoroacetic acid.
| 【1】 Lowe, R.F.; Lipshutz, B.H.; Stevens, K.L.; A novel route to the anti-HIV nucleoside d4T. Tetrahedron Lett 1995, 36, 16, 2711. |
| 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) | 12204 | 5-Methyl-2,4(1H,3H)-pyrimidinedione; Thymine | 65-71-4 | C5H6N2O2 | 详情 | 详情 |
| (II) | 12241 | (2R,3S)-2-(Hydroxymethyl)-5-methoxytetrahydro-3-furanol | C6H12O4 | 详情 | 详情 | |
| (III) | 12242 | 5-Bromo-6-[((2R,3S)-3-[[tert-butyl(diphenyl)silyl]oxy]-5-methoxytetrahydro-2-furanyl)methoxy]-5-methyldihydro-2,4(1H,3H)-pyrimidinedione | C27H35BrN2O6Si | 详情 | 详情 | |
| (IV) | 12243 | (1R,10R,11S)-6-Bromo-11-[[tert-butyl(diphenyl)silyl]oxy]-6-methyl-8,13-dioxa-2,4-diazatricyclo[8.2.1.0(2,7)]tridecane-3,5-dione | C26H31BrN2O5Si | 详情 | 详情 | |
| (V) | 12244 | (1R,10R,11S)-6-Bromo-11-hydroxy-6-methyl-8,13-dioxa-2,4-diazatricyclo[8.2.1.0(2,7)]tridecane-3,5-dione | C10H13BrN2O5 | 详情 | 详情 | |
| (VI) | 12161 | Thymidine; 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | 50-89-5 | C10H14N2O5 | 详情 | 详情 |