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Chemical Structure| 186046-78-6
Chemical Structure| 186046-78-6
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CAS No. :186046-78-6 MDL No. :MFCD09261301
Formula : C20H17N3O5 Boiling Point : -
Linear Structure Formula :- InChI Key :VPWKJWIKZUONJA-UHFFFAOYSA-N
M.W : 379.37 Pubchem ID :15513042
Synonyms :

Safety of [ 186046-78-6 ]

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 [ 186046-78-6 ]

* 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.

  • Upstream synthesis route of [ 186046-78-6 ]
  • Downstream synthetic route of [ 186046-78-6 ]

[ 186046-78-6 ] Synthesis Path-Upstream   1~3

  • 1
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  • [ 186046-78-6 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 23, p. 4445 - 4447
[2] European Journal of Organic Chemistry, 2008, # 18, p. 3141 - 3148
  • 2
  • [ 91-01-0 ]
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YieldReaction ConditionsOperation in experiment
22.1 g
Stage #1: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide
Stage #2: at 60℃; for 19.5 h;
Stage #3: With lithium hydroxide monohydrate In methanol; ethanol; water; acetonitrile at 0℃;
Cytosine (10.3 g, 90 mmol, 1.0 eq) was dissolved in DMF (90 mL).Potassium tert-butoxide (11.6 g, 103.5 mmol, 1.15 eq) was added.Thereafter, the reaction system was heated to 100 ° C for 2 hours.Cooling the reaction system to 10 ° C,Drop by drop in 30 minutesBenzyl 2-bromoacetate(16.05mL, 101mmol, 1.12eq),After the completion of the dropwise addition, the reaction system was warmed to room temperature and the reaction was continued for 12 hours.Add acetic acid (5.9 mL, 103.5 mmol, 1.2 eq) to quench the reaction.The reaction solution was spun dry.The residue was resuspended in H2O (100 mL).Continue stirring for 4 hours and then filter.Washed with H2O (4x 150mL),Cytosine-1-benzylacetic acid20.6g.Cytosine-1-benzylacetic acid (20.6 g, 82 mmol, 1.0 eq) was dissolved in DMF (160 mL).N,N'-carbonyldiimidazole (21.25 g, 131.25 mmol, 1.6 eq) was added.After the TLC detection reaction was completed, methanol was added.Continue to stir for 1.5 hours.Diphenylmethanol (19.65 g, 106.5 mmol, 1.3 eq) was added.The reaction system is heated to 60 ° C,After two batchesDiphenylmethanol (2 x 1.825 g, 9.9 mmol, 0.12 eq) was added at 1 hour intervals.Continue to react for 6 hours.Stop heating for 12 hours,The reaction was quenched by the addition of methanol (4.65 g, 115 mmol, 1.4 eq).Spin the reaction solution,The residue continues to recrystallize with ethanol,After recrystallization from methanol (100 mL), (4-N-(diphenylmethoxycarbonyl)-cytosyl)-1-acetate29.35g.Taking (4-N-(diphenylmethoxycarbonyl)-cytosine)-1-acetate29.35 g, 62.5 mmol, 1.0 eq) in a mixed solution of acetonitrile: MeOH:H 2 O: EtOH (2:2:1:1, 350 mL),Heating to dissolve the compound,After cooling to 0 ° C,An aqueous solution (196.8 mL) of LiOH.H 2 O (25.5 g, 0.61 mol, 9.7 eq) was added.TLC detected that the reaction was complete and then added citric acid (58.5 g,An aqueous solution (290 mL) of 303.5, 4.9 eq) was quenched.Obtaining (4-N-(diphenylmethoxycarbonyl)-cytosine)-1-acetic acid22.1g.
Reference: [1] Patent: CN108478807, 2018, A, . Location in patent: Paragraph 0023; 0053; 0077; 0078
  • 3
  • [ 211321-08-3 ]
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Reference: [1] Organic Letters, 2003, vol. 5, # 23, p. 4445 - 4447
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