6H-PURIN-6-ONE, 1,9-DIHYDRO-9-[3-[[(4-METHOXYPHENYL)DIPHENYLMETHOXY]METHYL]-4-[[(4-METHYLPHENYL)SULFONYL]OXY]BUTYL]-2-[[(4-METHOXYPHENYL)DIPHENYLMETHYL]AMINO]- synthesis
- Product Name:6H-PURIN-6-ONE, 1,9-DIHYDRO-9-[3-[[(4-METHOXYPHENYL)DIPHENYLMETHOXY]METHYL]-4-[[(4-METHYLPHENYL)SULFONYL]OXY]BUTYL]-2-[[(4-METHOXYPHENYL)DIPHENYLMETHYL]AMINO]-
- CAS Number:206067-84-7
- Molecular formula:C57H53N5O7S
- Molecular Weight:952.12
![6H-Purin-6-one, 1,9-dihydro-9-[4-hydroxy-3-[[(4-methoxyphenyl)diphenylmethoxy]methyl]butyl]-2-[[(4-methoxyphenyl)diphenylmethyl]amino]-](/CAS/20210111/GIF/97845-77-7.gif)
Yield:206067-84-7 55.1%
Reaction Conditions:
with pyridine at 0 - 20; for 0.5 h;Inert atmosphere;
Steps:
4.2.3. N2-(p-Anisyldiphenylmethyl)-9-[3-(p-anisyldiphenylmethoxymethyl)-4-tosyloxybutyl]guanine (9)
To a solution of the penciclovir derivative 7 (254 mg, 0.32 mmol) inpyridine (4 mL) at 0 °C, under argon, was added p-toluenesulfonylchloride (182 mg, 0.96 mmol). The solution was stirred at 0 °C for30 min and then at room temperature overnight. The dark yellow reactionmixture was quenched with ice-water and the solution wasevaporated in a rotary evaporator. The residual pyridine from the reactionmixture was removed by co-evaporation with toluene underreduced pressure. The oily residue of the crude product was purified byflash chromatography on silica gel (40 g) with CH2Cl2/MeOH gradient(0-4% MeOH) eluent to give the product 9 (167 mg, 55.1% yield) as a white solid. 1H NMR (600 MHz, DMSO-d6): δ 1.15 (m, 2H, CH2), 1.46(m, 1H, CH), 2.38 (s, 3H, Ar-CH3 of Ts), 2.64 (dd, J = 9.6 and 7.7 Hz,1H, CH2OMMTr), 2.74 (dd, J = 9.6 and 4.5 Hz, 1H, CH2OMMTr), 3.29(t, J =7.1 Hz, 2H, NCH2), 3.64 (s, 3H, OCH3 of N-MMTr), 3.74 (s, 3H,OCH3 of O-MMTr), 3.73 (m, 1H, CH2OTs), 3.84 (dd, J = 9.7 and5.2 Hz, 1H, CH2OTs), 6.75 (d, J =8.7 Hz, 2H, H-3′/H-5′ of CH3OPh-CN),6.88 (d, J = 8.8 Hz, 2H, H-3′/H-5′ of CH3OPh-C-O), 7.02-7.38 (m,24H, Ar-H), 7.45 (d, J =8.4 Hz, 2H, H-3/H-5 of Ts), 7.72 (d,J = 8.4 Hz, 2H, H-2/H-6 of Ts), 7.44 (s, 1H, H-8), 7.60 (s, 1H, N2-H),10.45 (s, 1H, N1-H); 13C NMR (150 MHz, DMSO-d6): δ 21.11 (CH3 ofTs), 27.15 (CH2), 36.07 (CH), 39.92 (NCH2), 54.92 (OCH3 of N-MMTr),55.04 (OCH3 of O-MMTr), 61.59 (CH2OMMTr), 69.56 (N-tC), 70.13(CH2OTs), 85.76 (O-tC), 112.78 (C3′/C5′ of CH3OPh-C-N), 113.16 (C3′/C5′ of CH3OPh-C-O), 117.02 (C5), 126.34, 126.87, 127.43 (Ph-C),127.54 (C2/C6 of Ts), 127.78, 127.81, 128.37, 128.40 (Ph-C), 129.81(C2′/C6′ of CH3OPh-C-O and CH3OPh-C-N), 130.14 (C3/C5 of Ts),132.03 (C1 of Ts), 134.93 (C1′ of CH3OPh-C-O), 136.93 (C1′ ofCH3OPh-C-N), 137.32 (C8), 144.08 and 144.23 (C1” of Ph-C-O), 144.76and 144.78 (C1” of Ph-C-N), 144.98 (C4 of Ts), 149.41 (C4), 150.45(C2), 156.57 (C6), 157.66 (C4′ of CH3OPh-C-N), 158.21 (C4′ ofCH3OPh-C-O); HRMS: Calcd for C57H54N5O7S (M + H): 952.3744;Found: 952.3532.
References:
Liu, Jie;Barrio, Jorge R.;Satyamurthy, Nagichettiar [Journal of Fluorine Chemistry,2017,vol. 201,p. 24 - 42]
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