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[ CAS No. 65844-74-8 ] {[proInfo.proName]}

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Chemical Structure| 65844-74-8
Chemical Structure| 65844-74-8
Structure of 65844-74-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 65844-74-8 ]

CAS No. :65844-74-8 MDL No. :MFCD27927075
Formula : C10H16O6 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 232.23 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 65844-74-8 ]

* 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 [ 65844-74-8 ]

[ 65844-74-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 65844-74-8 ]
  • [ 19013-37-7 ]
YieldReaction ConditionsOperation in experiment
93% With sodium chloride In water; dimethyl sulfoxide for 4.5h; Heating;
  • 2
  • [ 65844-74-8 ]
  • [ 3473-63-0 ]
  • [ 1092460-40-6 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: methanimidamide monoacetate With sodium methoxide In methanol at 23℃; for 0.333333h; Inert atmosphere; Stage #2: trimethyl 2-methylpropane-1,1,3-tricarboxylate In methanol at 25℃; for 18h; Inert atmosphere;
86.9% With sodium methoxide In methanol at 20℃; for 16h; Inert atmosphere; 4 Example 4 Methyl 3-(4,6-dihydroxypyrimidin-5-yl)butanoate A 12-L, 4-necked reactor, equipped with a mechanical stirrer, was charged with 2.80 L of methanol and sparged with nitrogen. The solvent was treated with NaOMe (1969 mL, 8612 mmol) and transfer washed with 250 mL of methanol. The mixture was left to stir for 1.5 hours before the solution was treated with formamidine acetate (246.6 g, 2368 mmol) in one sum (granular-homogenized). The mixture was allowed to stir for 20 minutes (the solids dissolved within about 10 minutes post addition) to afford a homogeneous solution. Trimethyl 2- methylpropane-l,l,3-tricarboxylate (500 g, 2153 mmol) was added via dropping funnel as a solution in 500 mL of methanol over a five minute period, followed by 200 mL more of methanol to complete transfer. The reaction (clear, bright yellow) was allowed to stir at ambient temperature overnight to completion as measured by NMR analysis (alliquot of 250 uL was removed via pipet and treated with five drops of aq. 3N HC1, reduced under vacuum to dryness, dissolved in d -DMSO and then filtered) after 16 hours. The reaction was placed in an ice-bath and cooled to about 3.1 °C over a one hour period. A three-pound bottle of HCl(g) was used to quench the reaction (bubbling gas into solution via teflon tubing) over a one hour ten minute period reaching an endpoint of about pH=2.5 (via paper). The temperature was maintained below about 9.6 °C throughout the addition, and the yellow solution changed to an off-white suspension. The suspension was concentrated using vacuum distillation (35-37 °C 200 Torr) of the methanol (removed 3.34 L) in vacuo to afford a white/tan paste. The mixture was suspended in 3.75 L of toluene (7.5X volume) and stirred for 30 minutes. The suspension was filtered off (table top filter/polypropylene cloth, pad washed with 2 X 500 mL portions of toluene). The pad of product was allowed to air-dry under suction overnight on the filter then broken up with a spatula to give 396.8 grams, 86.9% yield.
Stage #1: methanimidamide monoacetate With sodium methoxide In methanol at -15 - 20℃; for 0.5h; Inert atmosphere; Stage #2: trimethyl 2-methylpropane-1,1,3-tricarboxylate In methanol at 20℃; for 12h; Inert atmosphere; 1.b b) methyl 3-(4,6-dihydroxypyrimidin-5-yl)butyrate Under protection of nitrogen, methanol solution of sodium methoxide (30 wt %) (97.55 g) was added to methanol (400 mL) at 20°C. Then the resulting solution was cooled to -15°C, and formamidine acetate (22.98 g) was added. The resulting reaction system was reacted for 30 min. Subsequently, trimethyl 2-methylpropane-1,1,3-tricarboxylate (45.72 g) was added dropwise, the temperature was slowly raised to 20°C, and the reaction was continued for 12 hours. After the reaction was completed, the reaction solution was cooled to 0°C, and 4 M hydrochloric acid was added to adjust the pH=2.The solvent was evaporated under reduced pressure, and then 100 mL of water was added at 0°C to obtain a solid precipitate. The solid was collected by suction filtration. The filter cake was washed with water (50 mL) and dried in vacuum to obtain 29.60 g of yellow solid, which was used directly in the next step without purification.1H NMR (400 MHz, DMSO-d6) δ (ppm) 11.62 (s, 2H) , 7.86 (s, 1H) , 3.53 (s, 3H) , 3.34-3.42 (m, 1H) , 2.58-2.70 (m, 2H) , 1.11 (d, J = 6.8 Hz, 3H).
With sodium methoxide In methanol

  • 3
  • [ 65844-74-8 ]
  • [ 1001180-21-7 ]
  • 4
  • [ 65844-74-8 ]
  • [ 1001264-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: Chromobacterium strain SC-YM-1 / aq. phosphate buffer / 19 h / 0 °C / pH 7 - 7.6 / Resolution of racemate; Microbiological reaction; Large scale 2.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 2.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 3.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 4.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 6.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 7.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 8.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 9.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 9.2: 20 h / 20 °C / Inert atmosphere; Large scale 10.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 11.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 12.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 12.2: 20 °C / pH > 12 / Large scale
Multi-step reaction with 13 steps 1.1: Chromobacterium strain SC-YM-1 / aq. phosphate buffer / 19 h / 0 °C / pH 7 - 7.6 / Resolution of racemate; Microbiological reaction; Large scale 2.1: sodium methylate / methanol / 2.5 h / 0 °C / Inert atmosphere; Large scale 2.2: 10 h / 0 - 25 °C / Inert atmosphere; Large scale 3.1: 2,6-dimethylpyridine; trichlorophosphate / toluene / 25 h / 50 - 70 °C / Inert atmosphere; Large scale 4.1: N-ethyl-N,N-diisopropylamine / methanol / 4 h / 50 °C / Inert atmosphere; Large scale 5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 15 h / 20 °C / Large scale 6.1: caesium carbonate / N,N-dimethyl-formamide / 15 h / 20 - 35 °C / Large scale 7.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / tetrahydrofuran / 50 h / 50 °C / 2844.39 Torr / Autoclave; Large scale 8.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere; Large scale 9.1: formic acid; 10% Pd/C / 2-methyltetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Large scale 9.2: 20 h / 20 °C / Inert atmosphere; Large scale 9.3: 2 h / 20 °C / Inert atmosphere; Large scale 10.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C / Large scale 11.1: hydrogenchloride / toluene; water / 2 h / 55 °C / Large scale 12.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Large scale 13.1: hydrogenchloride / toluene; water / 1 h / 50 °C / Large scale 13.2: 20 °C / pH > 12 / Large scale
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