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[ CAS No. 4546-70-7 ] {[proInfo.proName]}

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Chemical Structure| 4546-70-7
Chemical Structure| 4546-70-7
Structure of 4546-70-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4546-70-7 ]

CAS No. :4546-70-7 MDL No. :MFCD00047240
Formula : C10H14N6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :NOLHIMIFXOBLFF-KVQBGUIXSA-N
M.W : 266.26 Pubchem ID :97188
Synonyms :

Calculated chemistry of [ 4546-70-7 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 4.0
Molar Refractivity : 65.92
TPSA : 145.33 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.92
Log Po/w (XLOGP3) : -0.52
Log Po/w (WLOGP) : -1.68
Log Po/w (MLOGP) : -1.64
Log Po/w (SILICOS-IT) : -2.2
Consensus Log Po/w : -1.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.38
Solubility : 11.1 mg/ml ; 0.0415 mol/l
Class : Very soluble
Log S (Ali) : -2.06
Solubility : 2.3 mg/ml ; 0.00864 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.04
Solubility : 244.0 mg/ml ; 0.916 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.72

Safety of [ 4546-70-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4546-70-7 ]

* 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.

  • Downstream synthetic route of [ 4546-70-7 ]

[ 4546-70-7 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 4546-70-7 ]
  • [ 17859-53-9 ]
  • [ 156549-47-2 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; chloro-trimethyl-silane 1.) pyridine, 40 deg C, 16 h; Yield given. Multistep reaction;
  • 2
  • [ 4546-70-7 ]
  • [ 106449-56-3 ]
YieldReaction ConditionsOperation in experiment
81% With acetic acid; sodium nitrite In water
59% With sodium nitrite In water; acetic acid for 0.0833333h;
  • 3
  • [ 4546-70-7 ]
  • [ 116113-30-5 ]
YieldReaction ConditionsOperation in experiment
40% With tri-n-butylaminophosphite In pyridine; N,N-dimethyl-formamide for 50h; Ambient temperature;
  • 4
  • [ 128790-76-1 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
79% With ammonium hydroxide at 55℃; for 38h;
  • 5
  • [ 961-07-9 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; ammonium hydroxide; trifluoroacetic anhydride 1. ice bath, 10 min, 2. cooling, 1.5 h; Yield given. Multistep reaction;
With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; ammonia; 1,1,1,3,3,3-hexamethyl-disilazane 1.) 10 h, 145 deg C; 2.) toluene, 48 h, 145 deg C; 3.) MeOH, H2O, 4 h, reflux; Yield given. Multistep reaction;
  • 6
  • [ 69256-45-7 ]
  • C22H22N6O4Si [ No CAS ]
  • [ 24638-90-2 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
With Na(1+)*O(3)H(1-) = NaO(3)H; trimethylsilyl trifluoromethanesulfonate 1) 3 h, reflux; Yield given. Multistep reaction;
  • 7
  • 2,6-diamino-8,2'-anhydro-8-mercapto-9-β-D-arabinofuranosylpurine [ No CAS ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
18% With nickel In water for 3h; Heating;
  • 8
  • [ 4546-70-7 ]
  • [ 701-99-5 ]
  • [ 156549-47-2 ]
YieldReaction ConditionsOperation in experiment
With water; triethylamine 1.) pyridine, RT, 90 min, 2.) RT, 3 h; Yield given. Multistep reaction;
  • 9
  • [ 951-78-0 ]
  • [ 1904-98-9 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
41% at 37℃; for 7h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.8;
  • 10
  • [ 4546-70-7 ]
  • [ 961-07-9 ]
YieldReaction ConditionsOperation in experiment
91% With adenosine aminohydrolase (EC 3.5.4.4) In dimethyl sulfoxide Ambient temperature; aq. sodium phosphate buffer (pH 7.4);
  • 11
  • [ 193885-47-1 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride 1.) toluene, 80 deg C, overnight, 2.) toluene, THF, 80 deg C, 3 h; Yield given. Multistep reaction;
  • 12
  • [ 2096-10-8 ]
  • [ 3608-57-9 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile); acetoxyisobutyryl bromide; ammonia; tri-n-butyl-tin hydride Yield given. Multistep reaction. Yields of byproduct given;
  • 13
  • [ 4546-70-7 ]
  • [ 4637-24-5 ]
  • N'-[6-(Dimethylamino-methyleneamino)-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-N,N-dimethyl-formamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide for 120h; Ambient temperature; Yield given;
YieldReaction ConditionsOperation in experiment
By following the procedure of part A and substituting for thymidine with the following: ... 2'-deoxyguanosine, 2'-deoxyuridine, 2'-deoxycytidine, uridine, 9-(2-deoxy-β-D-erythro-pentofuranosyl)2,6-diaminopurine, 1-(2-deoxy-β-D-erythro-pentofuranosyl)5-trifluoromethyl-2,4-dioxopyrimidine, 9-(2-deoxy-β-D-erythro-pentofuranosyl)2-aminopurine, 1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-fluoro-2,4-dioxopyrimidine, ...
  • 15
  • [ 4546-70-7 ]
  • N2-(phenoxyacetyl)-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine-2,6-diamine [ No CAS ]
  • 16
  • [ 4546-70-7 ]
  • [ 961-07-9 ]
YieldReaction ConditionsOperation in experiment
93.8% With sodium hydroxide; tris(hydroxymethyl)methylamine hydrochloride In water monomer at 40℃; for 13h; Enzymatic reaction; 4.2 (2) Synthesis of 2'-deoxyguanosine To the reaction mixture (1 mL) obtained in (1) above, 20% sodium hydroxide (10 μL), 1 mol/L Tris-HCl buffer (pH 7.0) (0.1 mL), and adenosine deaminase (50 units/mL) were sequentially added, and the mixture was incubated at 40° C. for 13 hours with stirring. As a result, 2'-deoxyguanosine (41.2 mmol/L) was synthesized from 2,6-diaminopurine-2'-deoxyriboside (43.9 mmol/L) (mole yield: 93.8%).
84% With adenosine deaminase In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 24h; Enzymatic reaction; 4.10. 2′-Deoxygunosine (2) ADA (1 g, 2.7 units/mg protein) was added to a solution of 3 (2.65 g,100 mmol) in DMSO (200 mL) and aqueous sodium phosphate buffer(0.1 mol/L, 2.5 L, pH = 7.4) and the mixture was stirred at room temperaturefor 24 h. Volatiles were evaporated in vacuo and the residue wasapplied to a column of Dowex 1 × 2 (OH-), which was washed sequentiallywith H2O, 80% MeOH-H2O and H2O. The product was then eluted(30 mmol/L aqueous Et3NH·HCO3) and fractions were evaporated severaltimes with H2O, and recrystallized from H2O to give 2 as a white solid(22 g, 84% yield).White solid. mp 252-254 °C (decomposition, lit.[23] 250-252 °C). 1HNMR (400 MHz, DMSO-d6) 10.78 (s, 1H, NH), 7.77 (s, 1H, 8-H), 6.53(s, 2H, NH2), 6.01 (d, J = 4.4 Hz, 1H, 1′-H), 5.69 (d, J = 4.8 Hz, 1H, 4′-H),5.59 (d, J = 2.0 Hz, 1H, OH), 4.04 (t, J = 4.0 Hz, 1H, 3′-H), 3.74 (d, J = 4.4 Hz,1H, 5′-H), 2.78-2.72 (m, 1H, 2′-H), 2.32-2.27 (m, 1H, 2′-H); 13C NMR(100 MHz, DMSO-d6) 156.9 (6-C), 156.6 (2-C), 151.0 (4-C), 136.9 (8-C),115.6 (5-C), 84.1 (1′-C), 83.3 (4′-C), 75.4 (3′-C), 60.9 (5′-C), 37.1 (2′-C);HRMS calcd for C10H14N5O4 [M + H]+ 268.1040, found 268.1040.
With sodium hydroxide; Tris-HCl buffer; E. coli adenosine deaminase In water monomer at 40℃; for 13h; Enzymatic reaction;
  • 17
  • [ 1904-98-9 ]
  • [ 50-89-5 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
70% With nucleoside deoxyribosyltransferase-II; sodium citrate at 40℃; for 42h; Enzymatic reaction;
at 40℃; for 16h; Enzymatic reaction; 4.1 Example 4; (1) Synthesis of 2,6-diaminopurine-2'-deoxyriboside; A solution (5 mL) containing thymidine (100 mmol/L) (product of YAMASA CORPORATION), 2,6-diaminopurine (50 mmol/L) (product of sigma), and nucleoside deoxyribosyl transferase II (0.385 units/mL) was incubated at 40° C. for 16 hours with stirring. As a result, 2,6-diaminopurine-2'-deoxyriboside was synthesized in an amount of 48.2 mmol/L.
With potassium phosphate; Geobacillus thermoglucosidasius purine nucleoside phosphorylase; Thermus thermophilus pyrimidine nucleoside phosphorylase In water at 70℃; for 1h; Enzymatic reaction;
  • 18
  • [ 4546-70-7 ]
  • [ 98-88-4 ]
  • [ 583047-61-4 ]
YieldReaction ConditionsOperation in experiment
76.3% Stage #1: 2-amino-2'-deoxyadenosine With pyridine; chloro-trimethyl-silane at 0℃; for 0.5h; Stage #2: benzoyl chloride With pyridine at 0℃; for 2h;
  • 19
  • [ 4546-70-7 ]
  • [ 776323-96-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C 13.1: aq. MeNH2 / methanol / 46 h / 20 °C 14.1: 0.38 g / 1,1'-carbonyldiimidazole / acetonitrile / 4 h / 20 °C
Multi-step reaction with 14 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C 13.1: 1.77 g / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 14.1: aq. MeNH2 / methanol / 20 °C
  • 20
  • [ 4546-70-7 ]
  • 3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-5-(2,6-diamino-purin-9-yl)-tetrahydro-furan-2-carbaldehyde oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C 13.1: aq. MeNH2 / methanol / 46 h / 20 °C
  • 21
  • [ 4546-70-7 ]
  • [ 776323-97-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: potassium tert-butoxide / tetrahydrofuran / 1.5 h / -40 °C 12.2: tetrahydrofuran / 2 h / -40 °C 13.1: 1.21 g / potassium tert-butoxide / tetrahydrofuran / 1 h / -40 °C 14.1: 0.70 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
  • 22
  • [ 4546-70-7 ]
  • C30H34N6O5Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C
  • 23
  • [ 4546-70-7 ]
  • [ 583047-62-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C
  • 24
  • [ 4546-70-7 ]
  • C31H36N6O6Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C
  • 25
  • [ 4546-70-7 ]
  • [ 583047-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C
  • 26
  • [ 4546-70-7 ]
  • C37H50N6O6Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C
  • 27
  • [ 4546-70-7 ]
  • C38H51BrN6O5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: potassium tert-butoxide / tetrahydrofuran / 1.5 h / -40 °C 12.2: tetrahydrofuran / 2 h / -40 °C
  • 28
  • [ 4546-70-7 ]
  • [ 583047-66-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C
  • 29
  • [ 4546-70-7 ]
  • C37H51N7O6Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C
  • 30
  • [ 4546-70-7 ]
  • [ 583047-63-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C
  • 31
  • [ 4546-70-7 ]
  • C51H54N6O7Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C
  • 32
  • [ 4546-70-7 ]
  • [ 583047-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C
  • 33
  • [ 4546-70-7 ]
  • C58H70N6O8Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C
  • 34
  • [ 4546-70-7 ]
  • [ 306305-12-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: potassium tert-butoxide / tetrahydrofuran / 1.5 h / -40 °C 12.2: tetrahydrofuran / 2 h / -40 °C 13.1: 1.21 g / potassium tert-butoxide / tetrahydrofuran / 1 h / -40 °C 14.1: 0.70 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 15.1: 87.7 percent / MeNH2 / methanol; H2O / 20 °C
  • 35
  • [ 4546-70-7 ]
  • 4'-C-cyano-2'-deoxyguanosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C 13.1: aq. MeNH2 / methanol / 46 h / 20 °C 14.1: 0.38 g / 1,1'-carbonyldiimidazole / acetonitrile / 4 h / 20 °C 15.1: 96.7 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C 16.1: 79.2 percent / adenosine deaminase; Tris-HCl buffer / 1 h / 40 °C / pH 7.50
Multi-step reaction with 16 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C 13.1: 1.77 g / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 14.1: aq. MeNH2 / methanol / 20 °C 15.1: 96.7 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C 16.1: 79.2 percent / adenosine deaminase; Tris-HCl buffer / 1 h / 40 °C / pH 7.50
  • 36
  • [ 4546-70-7 ]
  • [ 583047-55-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C 13.1: aq. MeNH2 / methanol / 46 h / 20 °C 14.1: 0.38 g / 1,1'-carbonyldiimidazole / acetonitrile / 4 h / 20 °C 15.1: 96.7 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C
Multi-step reaction with 15 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C 13.1: 1.77 g / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 14.1: aq. MeNH2 / methanol / 20 °C 15.1: 96.7 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C
  • 37
  • [ 4546-70-7 ]
  • [ 583047-67-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: hydroxylamine hydrochloride; pyridine / 0.5 h / 20 °C 13.1: 1.77 g / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C
  • 38
  • [ 4546-70-7 ]
  • [ 676458-04-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: chlorotrimethylsilane; pyridine / 0.5 h / 0 °C 1.2: 76.3 percent / pyridine / 2 h / 0 °C 2.1: pyridine / 3 h / 20 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 28.8 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.25 h / 0 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 2 h / 20 °C 6.1: NaOH / dioxane; H2O / 3 h / 20 °C 7.1: 30.83 g / NaBH4 / ethanol / 0.5 h / 0 °C 8.1: 60.3 percent / triethylamine / dimethylformamide / 1 h / 20 °C 9.1: imidazole / dimethylformamide / 20 °C 10.1: 17.5 g / p-toluenesulfonic acid hydrate / CHCl3; methanol / 0.33 h / 0 °C 11.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; pyridine; trifluoroacetic acid / toluene; dimethylsulfoxide / 1 h / 20 °C 12.1: potassium tert-butoxide / tetrahydrofuran / 1.5 h / -40 °C 12.2: tetrahydrofuran / 2 h / -40 °C 13.1: 1.21 g / potassium tert-butoxide / tetrahydrofuran / 1 h / -40 °C
  • 39
  • [ 4546-70-7 ]
  • N'-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-2,9-dihydro-1H-purin-6-yl]-N,N-diisobutyl-formamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / AcOH, NaNO2 / H2O 2: 96 percent / dimethylformamide / 6.5 h / Ambient temperature
  • 40
  • [ 4546-70-7 ]
  • N,N-Diisobutyl-N'-[2-oxo-9-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2,9-dihydro-1H-purin-6-yl]-formamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / AcOH, NaNO2 / H2O 2: 96 percent / dimethylformamide / 6.5 h / Ambient temperature 3: 77 percent / Et3N / tetrahydrofuran / 15 h / Ambient temperature
  • 41
  • [ 4546-70-7 ]
  • 2'-deoxy-N6-[(diisobutylamino)methylidene]-O2-(diphenylcarbamoyl)isoguanosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 81 percent / AcOH, NaNO2 / H2O 2: 96 percent / dimethylformamide / 6.5 h / Ambient temperature 3: 77 percent / Et3N / tetrahydrofuran / 15 h / Ambient temperature 4: 75 percent / pyridine, (i-Pr)2EtN / 4 h / Ambient temperature 5: 89 percent / 1M Bu4NF / tetrahydrofuran / 1.5 h / Ambient temperature
  • 42
  • [ 4546-70-7 ]
  • Diphenyl-carbamic acid 6-(diisobutylamino-methyleneamino)-9-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 81 percent / AcOH, NaNO2 / H2O 2: 96 percent / dimethylformamide / 6.5 h / Ambient temperature 3: 77 percent / Et3N / tetrahydrofuran / 15 h / Ambient temperature 4: 75 percent / pyridine, (i-Pr)2EtN / 4 h / Ambient temperature
  • 43
  • [ 4546-70-7 ]
  • 2'-deoxy-N6-[(diisobutylamino)methylidene]-5'-O-(4,4'-dimethoxytrityl)-O2-(diphenylcarbamoyl)isoguanosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 81 percent / AcOH, NaNO2 / H2O 2: 96 percent / dimethylformamide / 6.5 h / Ambient temperature 3: 77 percent / Et3N / tetrahydrofuran / 15 h / Ambient temperature 4: 75 percent / pyridine, (i-Pr)2EtN / 4 h / Ambient temperature 5: 89 percent / 1M Bu4NF / tetrahydrofuran / 1.5 h / Ambient temperature 6: 76 percent / 4-(dimethylamino)pyridine, Et3N / pyridine / 4.5 h / Ambient temperature
  • 44
  • [ 4546-70-7 ]
  • Diphenyl-carbamic acid 9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-tetrahydro-furan-2-yl}-6-(diisobutylamino-methyleneamino)-9H-purin-2-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 81 percent / AcOH, NaNO2 / H2O 2: 96 percent / dimethylformamide / 6.5 h / Ambient temperature 3: 77 percent / Et3N / tetrahydrofuran / 15 h / Ambient temperature 4: 75 percent / pyridine, (i-Pr)2EtN / 4 h / Ambient temperature 5: 89 percent / 1M Bu4NF / tetrahydrofuran / 1.5 h / Ambient temperature 6: 76 percent / 4-(dimethylamino)pyridine, Et3N / pyridine / 4.5 h / Ambient temperature 7: 73.9 percent / N,N-diisopropylethylamine / CH2Cl2 / 0.5 h / Ambient temperature
  • 45
  • [ 87791-88-6 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: DMAP / acetonitrile / 1 h / Ambient temperature 2: 1.) AIBN, Bu3SnH, 2.) TBAF / 1.) toluene, 80 deg C, overnight, 2.) toluene, THF, 80 deg C, 3 h
  • 46
  • [ 2096-10-8 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / pyridine / 6 h / Ambient temperature 2: DMAP / acetonitrile / 1 h / Ambient temperature 3: 1.) AIBN, Bu3SnH, 2.) TBAF / 1.) toluene, 80 deg C, overnight, 2.) toluene, THF, 80 deg C, 3 h
Multi-step reaction with 4 steps 1: 92 percent / saturated bromine-water / 1 h / Ambient temperature 2: 1.) dibutyltin oxide, 2.) triethylamine / 1.) methanol, 5 h, reflux, 2.) methanol, 1 h, room temperature 3: 88 percent / 40 percent sodium hydrogensulfide aq. / dimethylformamide / 6 h / 60 °C 4: 18 percent / Raney nickel / H2O / 3 h / Heating
  • 47
  • [ 4546-70-7 ]
  • 5'-O-dimethoxytrityl-N2,N6-bis(phenoxyacetyl)-2,6-diaminopurine-2'-deoxyriboside 3'-O-succinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) trimethylsilyl chloride, 2.) aq. ammonia / 1.) pyridine, 40 deg C, 16 h 2: 26 percent / pyridine / 4 h / Ambient temperature 3: 60 percent / DMAP / CH2Cl2 / 16 h
Multi-step reaction with 3 steps 1: 2.) triethylamine, water / 1.) pyridine, RT, 90 min, 2.) RT, 3 h 2: 26 percent / pyridine / 4 h / Ambient temperature 3: 60 percent / DMAP / CH2Cl2 / 16 h
  • 48
  • [ 4546-70-7 ]
  • [ 156549-48-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) trimethylsilyl chloride, 2.) aq. ammonia / 1.) pyridine, 40 deg C, 16 h 2: 26 percent / pyridine / 4 h / Ambient temperature
Multi-step reaction with 2 steps 1: 2.) triethylamine, water / 1.) pyridine, RT, 90 min, 2.) RT, 3 h 2: 26 percent / pyridine / 4 h / Ambient temperature
  • 49
  • [ 4546-70-7 ]
  • 5'-O-dimethoxytrityl-N2,N6-bis(phenoxyacetyl)-2,6-diaminopurine-2'-deoxyriboside 3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) trimethylsilyl chloride, 2.) aq. ammonia / 1.) pyridine, 40 deg C, 16 h 2: 26 percent / pyridine / 4 h / Ambient temperature 3: 44 percent / ethyldiisopropylamine / CH2Cl2 / 1 h
Multi-step reaction with 3 steps 1: 2.) triethylamine, water / 1.) pyridine, RT, 90 min, 2.) RT, 3 h 2: 26 percent / pyridine / 4 h / Ambient temperature 3: 44 percent / ethyldiisopropylamine / CH2Cl2 / 1 h
  • 50
  • [ 4546-70-7 ]
  • 6-amino-9-<2-deoxy-3,5-bis-O-(2-methylpropanoyl)-β-D-erythro-pentofuranosyl>-1,9-dihydro-2H-purin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / NaNO2 / acetic acid; H2O / 0.08 h 2: 44 percent / pyridine / 1 h / Ambient temperature
  • 51
  • [ 4546-70-7 ]
  • 6-amino-9-<2-deoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-β-D-erythro-pentofuranosyl>-1,9-dihydro-2H-purin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / NaNO2 / acetic acid; H2O / 0.08 h 2: 57 percent / 1H-imidazole / dimethylformamide / 12 h
  • 52
  • 2,6-Bis(aminobenzoyl)purin [ No CAS ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / Heating 2: 1) trimethylsilyltrifluormethansulfonate, 2) NaOH3 / 1) 3 h, reflux
  • 53
  • [ 81102-44-5 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) dibutyltin oxide, 2.) triethylamine / 1.) methanol, 5 h, reflux, 2.) methanol, 1 h, room temperature 2: 88 percent / 40 percent sodium hydrogensulfide aq. / dimethylformamide / 6 h / 60 °C 3: 18 percent / Raney nickel / H2O / 3 h / Heating
  • 54
  • [ 81102-48-9 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 45 percent / ammonia gas / methanol / 15 h / 100 °C 2: 18 percent / Raney nickel / H2O / 3 h / Heating
  • 55
  • N2,3',5'-O-triacetyl-8,2'-S-cycloguanosine [ No CAS ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: phosphoryl chloride, N,N-diethylaniline / 0.08 h / Heating 2: 45 percent / ammonia gas / methanol / 15 h / 100 °C 3: 18 percent / Raney nickel / H2O / 3 h / Heating
  • 56
  • [ 37070-11-4 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 88 percent / pyridine / 48 h / Ambient temperature 2: phosphoryl chloride, N,N-diethylaniline / 0.08 h / Heating 3: 45 percent / ammonia gas / methanol / 15 h / 100 °C 4: 18 percent / Raney nickel / H2O / 3 h / Heating
  • 57
  • 2',3',5'-tri-O-acetyl-2-chloroadenosine [ No CAS ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 54 percent / ammonia gas / ethanol / 10 h / 100 °C 2: 92 percent / saturated bromine-water / 1 h / Ambient temperature 3: 1.) dibutyltin oxide, 2.) triethylamine / 1.) methanol, 5 h, reflux, 2.) methanol, 1 h, room temperature 4: 88 percent / 40 percent sodium hydrogensulfide aq. / dimethylformamide / 6 h / 60 °C 5: 18 percent / Raney nickel / H2O / 3 h / Heating
  • 58
  • [ 81102-46-7 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / 40 percent sodium hydrogensulfide aq. / dimethylformamide / 6 h / 60 °C 2: 18 percent / Raney nickel / H2O / 3 h / Heating
YieldReaction ConditionsOperation in experiment
192 mg (34%) IV Production of 2,6-diamino-9-(2-deoxy-Beta-D-erythro-pentofuranosyl)purine. EXAMPLE IV Production of 2,6-diamino-9-(2-deoxy-Beta-D-erythro-pentofuranosyl)purine. To 2 mmol of deoxyguanosine, dried by evaporation of pyridine and suspended in 20 mL of dry pyridine was added dropwise 2.3 mL (16 mmol) of trifluoroacetic anhydride, with cooling in an ice bath. After ten minutes 20 mL of cold, concentrated aqueous ammonia was added. After a further 11/2 hours the mixture was evaporated to dryness, the residue dissolved in water and the solution filtered through a 100 mL portion of Bio Rad AG 1-X2, hydroxide from resin to remove colored impurities. The resin was washed with 40% methanol in water to elute crude 2,6-diamino-9-(2-deoxy-Beta-D-erythro-pentofuranosyl)purine, which was further purified on the reversed-phase column described above using a gradient of 2-15% acetonitrile in water. Evaporation of appropriate fractions gave 192 mg (34%) of 2,6-diamino-9-(2-deoxy-D-erythro-pentofuranosyl)purine, a sample crystallized from water gave a mp of 148°. UVmax (MeOH) 282 nm, UVmin 256 nm; 1 H NMR (DMSO-d6) delta (ppm) 7.91 (s, 1,H8), 6.73 (br s, 2, NH2), 6.17 ("t", 1, Japp =6 Hz, H1'), 5.73 (br s, 2, NH2), 5.25 (m, 2, 3'-OH & 5'-OH), 4.35 (m, 1, H3'), 3.84 (m, 1, H4'), 3.54 (m,2,H5',5"), 2.59 & 2.17 (m & m, 1 & 1, H2' & H2"). Anal. Calcd. for C10 H14 N6 O3.H2 O: C, 42.25; H, 5.67; N, 29,56. Found: C, 42.54; H, 5.33; N, 29.56.
  • 60
  • 9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-2,6-di-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine [ No CAS ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
With ammonia In 1,4-dioxane; water at 55℃; for 8h; Inert atmosphere;
  • 61
  • [ 4546-70-7 ]
  • [ 1910-42-5 ]
  • C10H14N6O3*C12H14N2(2+)*2Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water at 20℃;
  • 62
  • [ 4546-70-7 ]
  • 9-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythropentofuranosyl]-N2,N6-diisobutyrylpurin-2,6-diamine 3′-(2-cyanoethyl)-N,N-diisopropylphosphoramidite [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane; pyridine / 0.25 h / 20 °C 1.2: 3.08 h / 20 °C 1.3: 0.5 h / 20 °C 2.1: pyridine / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C
  • 63
  • [ 4546-70-7 ]
  • 9-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythropentofuranosyl]-N2,N6-diisobutyrylpurin-2,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane; pyridine / 0.25 h / 20 °C 1.2: 3.08 h / 20 °C 1.3: 0.5 h / 20 °C 2.1: pyridine / 20 °C
  • 64
  • [ 4546-70-7 ]
  • [ 513-36-0 ]
  • 9-(2-deoxy-β-D-erythropentofuranosyl)-N2,N6-diisobutyrylpurin-2,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 2-amino-2'-deoxyadenosine With pyridine; chloro-trimethyl-silane at 20℃; for 0.25h; Stage #2: isobutyryl chloride at 20℃; for 3.08333h; Stage #3: With ammonia In water at 20℃; for 0.5h;
  • 65
  • [ 951-78-0 ]
  • [ 1904-98-9 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
96% With purine nucleoside phosphorylase; uridine phosphorylase In aq. phosphate buffer; dimethyl sulfoxide at 60℃; for 5h; Enzymatic reaction; 12.1 Assays were performed in 5 and 10% of aprotic dipolar co-solvents, at 60°C, twelve units/ml cell lysate wereadded to 150 ml of a solution kept thermostatically at 60 °C, and having the following composition of substrate solutions:1. 15 mM Uridine/2’-Deoxyuridine,2. 5 mM 2,6-Diaminopurine, and3. 30 mM potassium phosphate buffer, pH 7.[0084] After 5 hours, the reaction mixture was filtered by centrifugation at 2000 3g for 30 min, at 4°C, through anAmicon ultra-4 Centrifugal Filter Devices (Millipore, Bedford, MA) with a 3000-Da cut-off, and the filtrate was recovered.In table 3, the production yields of 2,6-Diaminopurine nucleosides prepared in the presence of co-solvents is shown.The resulting 2,6-Diaminopurine nucleosides (2,6-Diaminopurine riboside or 2,6-Diaminopurine deoxyriboside) wereanalyzed by HPLC. In these reactions, the products were obtained in high yields (over 80%).
  • 66
  • [ 38925-80-3 ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / ethanol; water / 0.5 h / Reflux 2: hydrogen; palladium 10% on activated carbon / ethanol; N,N-dimethyl acetamide / 24 h / 20 °C 3: potassium carbonate / methanol / 1 h / 20 °C
  • 67
  • C26H26N6O5 [ No CAS ]
  • [ 4546-70-7 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In methanol at 20℃; for 1h;
  • 68
  • [ 4546-70-7 ]
  • C10H13N6O12P3(4-)*2H(1+)*2Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: 2-amino-2'-deoxyadenosine With trimethyl phosphite; trichlorophosphate at 0℃; for 3h; Stage #2: With tributyl-amine; O7P2(4-)*C12H27N*4H(1+) In N,N-dimethyl-formamide at 0℃; for 1h; Stage #3:
  • 69
  • [ 4546-70-7 ]
  • 2-amino-2',5'-dideoxy-5'-iodoadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With pyridine; iodine; triphenylphosphine at 20℃; for 4h; 27 Iodine (14.3 g, 56.3 mmol) was added to a pyridine (100 mL) solution of 2-Amino-2'-deoxyadenosine (10.0 g, 37.6 mmol) and triphenylphosphine (14.8 g, 56.3 mmol) Stirring was carried out at room temperature. After 4 hours, a 10% aqueous sodium thiosulfate solution was added to the reaction solution and the mixture was distilled off under reduced pressure. Then, 100 mL of dichloromethane and 100 mL of water were added to the residue, and the mixture was stirred on an ice bath. Thereafter, the precipitate was collected by filtration and vacuum dried at 40 ° C. to obtain compound 48 (11.7 g, 31.1 mmol, 83%).
  • 70
  • [ 4546-70-7 ]
  • 2-amino-9-(2,5-dideoxy-beta-D-glycero-pent-4-enoufranosyl)adenine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: iodine; triphenylphosphine; pyridine / 4 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 80 °C
  • 71
  • [ 4546-70-7 ]
  • 2-amino-4'-azido-2',5'-dideoxy-5'-iodoadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: iodine; triphenylphosphine; pyridine / 4 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 80 °C 3: sodium azide; Iodine monochloride / N,N-dimethyl-formamide / 1 h / 20 °C
  • 72
  • [ 4546-70-7 ]
  • 2-amino-4'-azido-3'-O-benzoyl-2',5'-dideoxy-5'-iodoadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: iodine; triphenylphosphine; pyridine / 4 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 80 °C 3: sodium azide; Iodine monochloride / N,N-dimethyl-formamide / 1 h / 20 °C 4: dmap; pyridine / 2 h / 20 °C
  • 73
  • [ 4546-70-7 ]
  • N<SUP>4</SUP>-acetyl-2-acetylamino-4'-azido-3'-O-benzoyl-2', 5'-dideoxy-5'-iodoadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: iodine; triphenylphosphine; pyridine / 4 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 80 °C 3: sodium azide; Iodine monochloride / N,N-dimethyl-formamide / 1 h / 20 °C 4: dmap; pyridine / 2 h / 20 °C 5: dmap; triethylamine; pyridine / 40 °C
  • 74
  • [ 4546-70-7 ]
  • 2-amino-4'-azido-2'-deoxyadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: iodine; triphenylphosphine; pyridine / 4 h / 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 80 °C 3.1: sodium azide; Iodine monochloride / N,N-dimethyl-formamide / 1 h / 20 °C 4.1: dmap; pyridine / 2 h / 20 °C 5.1: dmap; triethylamine; pyridine / 40 °C 6.1: 3-chloro-benzenecarboperoxoic acid; 3-chlorobenzoate; tetra(n-butyl)ammonium hydrogensulfate; dipotassium hydrogenphosphate / water; dichloromethane / 3 h / 0 - 20 °C 6.2: 50 °C / Sealed tube
  • 75
  • [ 4546-70-7 ]
  • 2-amino-2'-deoxy-8-(phenylethynyl)adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bromine; sodium acetate / acetic acid / 3.5 h / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2.5 h / 65 °C / Inert atmosphere
  • 76
  • [ 4546-70-7 ]
  • 2'-deoxy-8-hex-1-yn-1-yl-2-oxo-2-hydroadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bromine; sodium acetate / acetic acid / 3.5 h / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2.5 h / 65 °C / Inert atmosphere 3: sodium nitrite; acetic acid / water; tetrahydrofuran / 4.5 h / 50 °C
  • 77
  • [ 4546-70-7 ]
  • C17H24N6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bromine; sodium acetate / acetic acid / 3.5 h / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2.5 h / 65 °C / Inert atmosphere 3: sodium nitrite; acetic acid / water; tetrahydrofuran / 4.5 h / 50 °C
  • 78
  • [ 4546-70-7 ]
  • 2'-deoxy-8-(3-hydroxy-3-methylbut-1-yn-1-yl)-2-oxo-2-hydroadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bromine; sodium acetate / acetic acid / 3.5 h / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2.5 h / 65 °C / Inert atmosphere 3: sodium nitrite; acetic acid / water; tetrahydrofuran / 4.5 h / 50 °C
  • 79
  • [ 4546-70-7 ]
  • 2'-deoxy-2-oxo-8-(3-phenylprop-1-yn-1-yl)-2-hydroadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bromine; sodium acetate / acetic acid / 3.5 h / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2.5 h / 65 °C / Inert atmosphere 3: sodium nitrite; acetic acid / water; tetrahydrofuran / 4.5 h / 50 °C
  • 80
  • [ 4546-70-7 ]
  • 2-amino-8-bromo-2'-deoxyadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With bromine; sodium acetate In acetic acid at 20℃; for 3.5h;
54% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 2h;
  • 81
  • [ 4546-70-7 ]
  • 2-amino-2'-deoxy-8-(hex-1-yn-1-yl)adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bromine; sodium acetate / acetic acid / 3.5 h / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2.5 h / 65 °C / Inert atmosphere
  • 82
  • [ 4546-70-7 ]
  • 2-amino-2'-deoxy-8-[3-(diethylamino)prop-1-yn-1-yl]adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bromine; sodium acetate / acetic acid / 3.5 h / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2.5 h / 65 °C / Inert atmosphere
  • 83
  • [ 4546-70-7 ]
  • 2-amino-2'-deoxy-8-(3-hydroxy-3-methylbut-1-yn-1-yl)adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bromine; sodium acetate / acetic acid / 3.5 h / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2.5 h / 65 °C / Inert atmosphere
  • 84
  • [ 890-38-0 ]
  • [ 1904-98-9 ]
  • [ 4546-70-7 ]
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