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[ CAS No. 88759-55-1 ]

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Chemical Structure| 88759-55-1
Chemical Structure| 88759-55-1
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CAS No. :88759-55-1 MDL No. :MFCD00080810
Formula : C4H7KO5 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :174.19 g/mol Pubchem ID :-
Synonyms :

Safety of [ 88759-55-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 88759-55-1 ]

  • Downstream synthetic route of [ 88759-55-1 ]

[ 88759-55-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 88759-55-1 ]
  • [ 88824-09-3 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: potassium (2R,3R)-2,3,4-trihydroxybutanoate With hydrogen bromide; glacial acetic acid at 10 - 20℃; for 24h; Stage #2: methanol at 20℃; for 26.5h; Reflux; 4.3. (2S, 3R)-Methyl 2, 4-dibromo-3-hydroxybutanoate (8) Potassium (2S,3R)-2,3,4-trihydroxybutanoate 7 (50 g,0.28 mol) was added to a solution of 33% HBr in acetic acid (600 mL) at 10° C. The mixture was stirred at room temperature for 24 h. To the resulting solution, methanol (750 mL) was added dropwise over 30 min at room temperature and stirred for 24 h at the same temperature. The potassium bromide salt was filtered off. The filtrate was refluxed for 2 h, and then concentrated under vacuumat 40° C. The resulting residue was dissolved in ethyl acetate (300 mL). The organic layer was washed with water (200 mL), Sat. NaHCO3 solution (100 mL), brine solution (100 mL), dried over Na2SO4, filtered, and evaporated the solvent to yield (2S,3R)-methyl 2,4-dibromo-3-hydroxybutanoate 8 (71 g, 89%) as an off white solid. [α]D25 22.1 (c 0.5, CH2Cl2), lit.17b [α]D20 44.4 (c 3.4, CHCl3); IR (KBr): 3645, 3512, 2956, 2846, 1888, 1762, 1798, 1623,1446, 1348, 1149, 1091 cm-1; 1H NMR (500 MHz, CDCl3): δ 4.72 (d, J 3.5 Hz, 1H), 4.18-4.15 (m, 1H), 3.84 (s, 3H), 3.53 (dd, J 10.5 Hz, 5.6 Hz, 1H), 3.49 (dd, J 10.5 Hz, 6.9 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 169.1, 70.6, 53.4, 48.6, 44.5, 32.9; MS (ESI): 275 [M+H]+, 277 [M+2H]+, 279 [M+4H]+.
83% Stage #1: potassium (2R,3R)-2,3,4-trihydroxybutanoate With hydrogen bromide; glacial acetic acid for 16h; Stage #2: methanol for 4h; Reflux; 1 Step 1. Synthesis of methyl (2S,3R)-2,4-dibromo-3-hydroxy-butanoate (C7) Potassium (2R,3R)-2,3,4-trihydroxybutanoate C6 (10 g, 57.1 mmol) was stirred with HBr in Acetic acid (154 g, 103 mL of 30% w/w, 570.8 mmol) for 16 h. Anhydrous MeOH (250 mL) was added and the mixture heated at reflux for 4 h. The mixture was concentrated dryness and the residue dissolved in EtOAc (100 mL). The solution was washed with water (50 mL) and brine (50 mL), then dried over Na2S04, and concentrated in vacuo. Purification by silica gel chromatography (Gradient: 15-20 % EtOAc in hexane) afforded the product as a colorless liquid (13 g, 83%). 'HNMR (400 MHz, CDCh) d 4.71 (d, J= 3.4 Hz, 1H), 4.17-4.14 (m, 1H), 3.82 (s, 3H), 3.53 - 3.44 (m, 2H).
83% Stage #1: potassium (2R,3R)-2,3,4-trihydroxybutanoate With hydrogen bromide; glacial acetic acid for 16h; Stage #2: methanol for 4h; Reflux; 1.A.1 Step 1. Synthesis of Methyl (2S,3R)-2,4-dibromo-3-hydroxy-butanoate (C7) Potassium (2R,3R)-2,3,4-trihydroxybutanoate C6 (10 g, 57.1 mmol) was stirred with HBr in Acetic acid (154 g, 103 mL of 30% w/w, 570.8 mmol) for 16 h. Anhydrous MeOH (250 mL) was added and the mixture heated at reflux for 4 h. The mixture was concentrated dryness and the residue dissolved in EtOAc (100 mL). The solution was washed with water (50 mL) and brine (50 mL), then dried over Na2SO4, and concentrated in vacuo. Purification by silica gel chromatography (Gradient: 15-20% EtOAc in hexane) afforded the product as a colorless liquid (13 g, 83%). 1H NMR (400 MHz, CDCl3) δ 4.71 (d, J=3.4 Hz, 1H), 4.17-4.14 (m, 1H), 3.82 (s, 3H), 3.53-3.44 (m, 2H).
83% Stage #1: potassium (2R,3R)-2,3,4-trihydroxybutanoate With hydrogen bromide; glacial acetic acid for 16h; Stage #2: methanol for 4h; Reflux; 1.1.1 Step 1. Synthesis of methyl (2S,3R)-2,4-dibromo-3-hydroxy-butanoate (C7) Potassium (2R,3R)-2,3,4-trihydroxybutanoate C6 (10 g, 57.1 mmol) was stirred with HBr in acetic acid (154 g, 103 mL of 30% w/w, 570.8 mmol) for 16 hours. Anhydrous MeOH (250 mL) was added and the mixture heated at reflux for 4 hours. The mixture was concentrated to dryness and the residue dissolved in EtOAc (100 mL). The solution was washed with water (50 mL) and brine (50 mL), then dried over Na2SC>4, and concentrated in vacuo. Purification by silica gel chromatography (Gradient: 15-20 % EtOAc in hexane) afforded the product as a colorless liquid (13 g, 83%). NMR (400 MHz, CDCb) d 4.71 (d, J= 3.4 Hz, 1H), 4.17-4.14 (m, 1H), 3.82 (s, 3H), 3.53 - 3.44 (m, 2H)
83% Stage #1: potassium (2R,3R)-2,3,4-trihydroxybutanoate With hydrogen bromide; glacial acetic acid for 16h; Stage #2: methanol for 4h; Reflux; 1.1 Step 1. Synthesis of methyl (2S,3R)-2,4-dibromo-3-hydroxy-butanoate (C2) Potassium (2R,3R)-2,3,4-trihydroxybutanoate Cl (10 g, 57.1 mmol) was stirred with HBr in acetic acid (154 g, 103 mL of 30%w/w, 570.8 mmol) for 16 hours. Anhydrous MeOH (250 mL) was added and the mixture heated at reflux for 4 hours. The mixture was concentrated to dryness and the residue dissolved in EtOAc (100 mL). The solution was washed with water (50 mL) and brine (50 mL), then dried over Na2SO4, and concentrated in vacuo. Purification by silica gel chromatography (Gradient: 15-20% EtOAc in hexane) afforded the product as a colorless liquid. Methyl (2S,3R)-2,4-dibromo-3-hydroxy-butanoate (13 g, 83%). 1H NMR (400 MHz, Chloroform -d) δ 4.71 (d, J= 3.4 Hz, 1H), 4.17-4.14 (m, 1H), 3.82 (s, 3H), 3.53-3.44 (m, 2H).
83% Stage #1: potassium (2R,3R)-2,3,4-trihydroxybutanoate With hydrogen bromide; glacial acetic acid for 16h; Stage #2: methanol for 4h; Reflux; 1.1 Step 1. Synthesis of methyl (2S,3R)-2,4-dibromo-3-hydroxy-butanoate (C2) Potassium (2R,3R)-2,3,4-trihydroxybutanoate Cl (10 g, 57.1 mmol) was stirred with HBr in acetic acid (154 g, 103 mL of 30%w/w, 570.8 mmol) for 16 hours. Anhydrous MeOH (250 mL) was added and the mixture heated at reflux for 4 hours. The mixture was concentrated to dryness and the residue dissolved in EtOAc (100 mL). The solution was washed with water (50 mL) and brine (50 mL), then dried over Na2SO4, and concentrated in vacuo. Purification by silica gel chromatography (Gradient: 15-20% EtOAc in hexane) afforded the product as a colorless liquid. Methyl (2S,3R)-2,4-dibromo-3-hydroxy-butanoate (13 g, 83%). 1H NMR (400 MHz, Chloroform -d) δ 4.71 (d, J= 3.4 Hz, 1H), 4.17-4.14 (m, 1H), 3.82 (s, 3H), 3.53-3.44 (m, 2H).
74% Stage #1: potassium (2R,3R)-2,3,4-trihydroxybutanoate With hydrogen bromide; glacial acetic acid at 20 - 65℃; for 46h; Stage #2: methanol With sulfuric acid In methanol for 6h; Reflux; 1.3.9 Step 9: methyl(2S,3R)-2,4-dibromo-3-hydroxybutyrate Synthesis The hydrogen bromide / acetic acid solution (33%, 2 liters) containing was added to (2R, 3R) -2,3,4- trihydroxybutylthio potassium (560 g, 3.21 mol) in a reactor. Stirred for 24 hours at room temperature, the reaction mixture was poured into dry methanol (14 liters), and then stirred for 18 hours at room temperature, then the reaction was heated to reflux for 4 hours 65°C . The reaction solution was concentrated under reduced pressure, water (1 liter) and ethyl acetate (1.5 liters) was extracted, the organic phase was separated, dried over sodium sulfate, and concentrated to give (2S, 3R) -2,4- dibromo-3-hydroxy butyric acid and (2S,3R)-2,4- dibromo-3-hydroxybutyrate as an oil mixture of methyl was 706 grams. Sulfuric acid (60 ml) was slowly added to the mixture (680 g) in methanol (3.5 l) was heated at reflux for 6 hours, TLC (PE: EA = 10: 1) plate the reaction was complete, the reaction mixture was concentrated, the residue dissolved in ethyl acetate (800 ml), washed with water (500 ml) was washed, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give the product as an off white solid (650 g, yield 74%).
With hydrogen bromide 1.) acetic acid, room temperature, 24 h, 2.) boiled, 2 h; Yield given. Multistep reaction;

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  • [ 908094-01-9 ]
  • [ 88759-55-1 ]
  • [ 89299-65-0 ]
YieldReaction ConditionsOperation in experiment
25% Stage #1: potassium (2R,3R)-2,3,4-trihydroxybutanoate With Dowex(R) 50X4-400; hydrogen cation In methanol at -20℃; for 0.25h; Stage #2: diazomethane In diethyl ether at -20℃; Further stages.;
  • 3
  • [ 10323-20-3 ]
  • [ 88759-55-1 ]
YieldReaction ConditionsOperation in experiment
48% With oxygen; potassium hydroxide; In methanol; water; at 45℃; for 62h; Under ice cooling, potassium hydroxide (1.12 kg, 19.98 moles) was slowly added to methanol (10 liters) and water (2.4 liters) of a mixed solvent, the temperature control does not exceed 45C . After addition, the oxygen fed to the reaction mixture until the reaction was reduced to 35C , solution of D-(-)-arabinose (1 kg, 6.66 mol, dissolved in 2.4 liters of water) of water, dropping over 6 hours (maintained throughout the course of the oxygen gas) and maintaining the reaction temperature at 35C . After the dropping, the oxygen was continuously fed for 2 hours and then air was 60 hours. The reaction solution was concentrated under reduced pressure to 2.4 l oil, and then oil was slowly added dropwise rapidly stirred methanol (10 liters), a large quantity of white solid was precipitated. After the dropwise addition, filtered, and dried in vacuo to give a white solid (560 g, yield 48%).
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