* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Compound 27:25 26 27[227] To a solution of 5-nitro-m-xylene-α,α'-diol 25 (1.07 g, 5.84 mmol) in methanol (50 mL) was added Pd/C (10percent, 311 mg, 0.29 mmol). Hydrogen was introduced to replace the air then the mixture was hydrogenated (H2, 5 psi) for 2 hours at room temperature. The solution was filtered through celite and the filtrate was evaporated by rotary evaporation in vacuo to give compound 26 as a white solid (900 mg, y = 100percent). 1H NMR (400 MHz, MeOD): δ 6.71 (s, IH), 6.66 (s, 2H), 4.51 (s, 4H); 13C NMR (400 MHz, MeOD): δ 148.9, 143.8, 116.7, 114.3, 65.5; It was dissolved in anhydrous acetonitrile (30 mL) and ethyl bromoacetate (443 μl, 4.67 mmol) and potassium carbonate (807 mg, 5.84 mmol) were added. The mixture was put in a 86 0C oil bath and refluxed for 17 hours. The reaction mixture was removed from the oil bath, cooled to room temperature and diluted with dichloromethane. It was filtered through celite and the solid was washed with dichloromethane. White precipitate appeared in the filtrate. It was col]ected by filtration to give compound 27 (414 mg, y = 39percent) as a white solid. 1H NMR (400 MHz, MeOD): δ 6.67 (s, IH), 6.53 (s, 2H), 4.51 (s, 4H), 3.94 (s, 2H), 3.73 (s, 3H); 13C NMR (400 MHz, MeOD): δ 174.0, 149.7, 143.9, 116.2, 111.6, 65.6, 52.6, 46.5; MS (m/z): found 248.0 (M + Na)+.
With lithium aluminium tetrahydride In tetrahydrofuran for 3 h; Reflux
A solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq L1AIH4 (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 percent).
70%
With lithium aluminium tetrahydride In tetrahydrofuran for 3 h; Reflux
A solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq L1AIH4 (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 percent).
Reference：
[1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 1, p. 161 - 171
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4350 - 4364
[3] Patent: WO2017/177326, 2017, A1, . Location in patent: Page/Page column 59; 64; 68
[4] Patent: WO2018/191278, 2018, A2, . Location in patent: Page/Page column 86; 90; 91; 94; 97
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7588 - 7594
[6] Journal of Medicinal Chemistry, 2010, vol. 53, # 9, p. 3480 - 3488
[7] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10405 - 10413
[8] Bulletin of the Chemical Society of Japan, 2008, vol. 81, # 8, p. 1012 - 1018
[9] Supramolecular Chemistry, 2018, vol. 30, # 10, p. 822 - 831
[10] Journal of the American Chemical Society, 2018, vol. 140, # 40, p. 13011 - 13021
3
[ 42122-73-6 ]
[ 71176-54-0 ]
Reference：
[1] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 30, p. 3622 - 3634
[2] Journal of the American Chemical Society, 1999, vol. 121, # 41, p. 9531 - 9538
[3] Nucleosides and Nucleotides, 1999, vol. 18, # 2, p. 291 - 305
[4] Canadian Journal of Chemistry, 2012, vol. 90, # 1, p. 138 - 144
4
[ 99-31-0 ]
[ 71176-54-0 ]
Reference：
[1] Synthesis, 1992, # 12, p. 1235 - 1236
[2] Canadian Journal of Chemistry, 2012, vol. 90, # 1, p. 138 - 144
[3] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 30, p. 3622 - 3634
5
[ 10560-13-1 ]
[ 71176-54-0 ]
Reference：
[1] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 535 - 544
<i>N</i>'-{9-[3-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-phenyl]-6-oxo-6,9-dihydro-1<i>H</i>-purin-2-yl}-<i>N</i>,<i>N</i>-dimethyl-formamidine[ No CAS ]
<i>N</i>-{9-[3-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-phenyl]-9<i>H</i>-purin-6-yl}-benzamide[ No CAS ]
succinic acid mono-{3-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[2-(dimethylamino-methyleneamino)-6-oxo-1,6-dihydro-purin-9-yl]-benzyl} ester[ No CAS ]
9-[3-[[(2-cyanoethoxy)(N,N-diisopropylamino)phosphinyl]oxymethyl]-5-(4,4'-dimethoxytrityloxymethyl)phenyl]-2-N-[(dimethylamino)methylene]guanine[ No CAS ]
(3R,5S,6E)-7-({5-[3-azido-5-(azidomethyl)benzyloxymethyl]-4-(4-fluorophenyl)-2,6-diisopropyl}pyridin-3-yl)-3,5-dihydroxy-6-heptenoic acid tert-butyl ester[ No CAS ]
(3R,5S,6E)-7-({5-[3-azido-5-(azidomethyl)benzyloxymethyl]-4-(4-fluorophenyl)-2,6-diisopropyl}pyridin-3-yl)-3,5-dihydroxy-3,5-O-isopropylidene-6-heptenoic acid tert-butyl ester[ No CAS ]
{3-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxymethyl]-benzyl}-carbamic acid 9<i>H</i>-fluoren-9-ylmethyl ester[ No CAS ]
Diisopropyl-phosphoramidous acid 3-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-methyl}-benzyl ester 2-cyano-ethyl ester[ No CAS ]
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