反应 #1365734

反应方程式

hydrazine hydrate

9-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)adenine

→

3

收率 68.0%

9-(3,5-Di-O-benzoyl-β-L-xylofuranosyl)adenine

收率 68.0%

溶剂

pyridine

反应条件

后处理

1. 1
   其他The reaction was quenched
2. 2
   workup.ADDITIONby adding acetone (40 mL)
3. 3
   workup.STIRRINGstirring
4. 4
   workup.ADDITIONdiluted with water (250 mL)
5. 5
   萃取extracted with chloroform (2×150 mL)
6. 6
   洗涤The organic layer was washed successively with an aqueous saturated solution of NaHCO3 (3×100 mL) and water (3×100 mL)
7. 7
   其他dried
8. 8
   过滤filtered
9. 9
   浓缩concentrated and co-evaporated with toluene and methanol
10. 10
    其他The residue was purified by silica gel column chromatography (0-3% MeOH in dichloromethane)

实验过程

A solution of 9-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)adenine 2 [Ref.: Gosselin, G.; Bergogne, M.-C.; Imbach, J.-L., “Synthesis and Antiviral Evaluation of β-L-Xylofuranosyl Nucleosides of the Five Naturally Occuring Nucleic Acid Bases”, Journal of Heterocyclic Chemistry, 1993, 30 (Oct.-Nov.), 1229-1233] (8.30 g, 16.05 mmol) and hydrazine hydrate 98% (234 mL, 48.5 mmol) in a mixture of pyridine/glacial acetic acid (4/1, v/v, 170 mL) was stirred at room temperature for 22 h. The reaction was quenched by adding acetone (40 mL) and stirring was continued for one additional hour. The reaction mixture was reduced to one half of its volume, diluted with water (250 mL) and extracted with chloroform (2×150 mL). The organic layer was washed successively with an aqueous saturated solution of NaHCO3 (3×100 mL) and water (3×100 mL), dried, filtered, concentrated and co-evaporated with toluene and methanol. The residue was purified by silica gel column chromatography (0-3% MeOH in dichloromethane) to give 3 (5.2 g, 68%) precipitated from diisopropylic ether: 1H NMR (DMSO-d6): δ4.5-4.9 (m, 4H, H-2′, H-4′, H-5′ and H-5″), 5.64 (t, 1H, H-3″, J2′,3′=J3′,4′=3.5 Hz), 6.3 (br s, 1H, OH-2′), 6.45 (d, 1H, H-1′, J1′,2′=4.6 Hz), 7.3 (br s, 2H, NH2-6), 7.4-7.9 (m, 10H, 2 benzoyls), 8.07 and 8.34 (2s, 2H, H-2 and H-8); ms: matrix G/T, (FAB+) m/z 476 [M+H]+, 136 [BH2]+, (FAB−) m/z 474 [M−H]−, 134 [B]−; UV (95% ethanol): λmax 257 nm (ε 16400), 230 nm (ε 29300), λmin 246 nm (ε 14800); [α]D20 =−64 (c 1.07, CHCl3). Anal. Calcd for C24H21N5O4 (M=475.45): C, 60.43; H, 4.45; N, 14.73. Found: C, 60.41; H, 4.68; N, 14.27.

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