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[ CAS No. 492-62-6 ]

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2D
Chemical Structure| 492-62-6
Chemical Structure| 492-62-6
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Quality Control of [ 492-62-6 ]

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Product Details of [ 492-62-6 ]

CAS No. :492-62-6MDL No. :MFCD00063774
Formula :C6H12O6Boiling Point :410.797°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :180.16Pubchem ID :79025
Synonyms :

1. alpha-D-Glucose

Computed Properties of [ 492-62-6 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 492-62-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 492-62-6 ]

  • Downstream synthetic route of [ 492-62-6 ]

[ 492-62-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 492-62-6 ]
  • [ 67-64-1 ]
  • [ 582-52-5 ]
YieldReaction ConditionsOperation in experiment
64.7% With sulfuric acid; for 6h;Cooling with ice; Using a 1 L round bottomflask, 30 g (0.17 mol) of anhydrous alpha-D-glucose was addedin 0.6 L of acetone. The mixture was stirred vigorously in an ice-water bath. Concentrated H2SO4 (30mL) was added dropwise for 6 hours. After all the acid was added, the solution was cooled to 0C and neutralized by 50% aqueous potassium hydroxide solution to maintain the pH of the solution near 7. After stirring overnight, thesolution was filtered, and the solvent was removed under reduced pressure. Thesolid was dissolved in 100 mL of dichloromethane and the solution was washed with100 mL of water. The aqueous phase was then extracted three times with 100 mL ofdichloromethane. The organic layers were combined and then concentrated underreduced pressure. Recrystallization from petroleumether gave 28 g of white crystals(64.7% yield).1H NMR (500 MHz, Chloroform-d) delta: 5.94 (d, J = 3.6 Hz, 1 H), 4.53 (d, J = 3.7 Hz, 1 H), 4.39-4.29 (m, 2H), 4.16 (dd, J = 8.7, 6.2 Hz, 1 H), 4.06 (dd,J = 7.6, 2.8 Hz, 1 H), 3.98 (dd, J = 8.6, 5.4 Hz, 1 H), 2.65 (d, J = 3.7 Hz, 1 H), 1.49 (s,3H), 1.44 (s, 3H), 1.36 (s, 3H), 1.31 (s, 3H). 13C NMR (126 MHz, Chloroform-d) delta:111.96, 109.79, 105.42, 85.22, 81.27, 75.34, 73.61, 67.80, 26.99, 26.90, 26.32, 25.28.
55% With sulfuric acid; copper(II) sulfate; at 0 - 20℃; for 30.16h; D-Glucose (30 g, 166.5 mmol) was added to dry acetone (600 mL) at room temperature and wasfollowed by anhydrous CuSO4 (30 g, 610.60 mmol). The reaction mixture was cooled to 0 C,and conc. H2SO4 (22 mL, 0.66 molar in acetone) was added drop-wise over a period of 10 min.The reaction mixture was stirred at room temperature for 30 h. After completion, (TLC) reaction mixture was neutralized with a saturated solution of K2CO3. The solution was filtered and thefiltrate was evaporated under reduced pressure. The residue thus obtained was extracted withchloroform and dried over anhydrous Na2SO4, concentrated under reduced pressure to afford ayellowish solid, which was recrystallized from chloroform: hexane (1:9) to to afford the productglucose-di-acetone (GDA) S9 (24 g, 55%) as white crystals.
42% With zinc(II) chloride;iodine; at 20℃; for 21h;Heating / reflux; To 305 g (1.69 mol) of powdered D-glucose in 2.5 L of acetone (99.9%) is added 500 g (3.67 mol) of anhydrous ZnCl2 and 12 g (0.047 mol) of iodine. The mixture is stirred for 16 hrs at RT and then 5 hrs at reflux. It is then neutralised with 50% NaOH solution (336 g in 330 mL) and addition of sodium thiosulphate solution (23 g). The precipitated salts are filtered off through celite and the precipitate washed with acetone three times. The acetone is evaporated and the residue redissolved in dichloromethane and washed with water two times. After drying with MgSO4 and evaporation of the organic phase the desired product is crystallised from boiling hexane. This yields 185.3 g (42%).
  • 2
  • [ 492-62-6 ]
  • [ 98-88-4 ]
  • [ 22415-91-4 ]
YieldReaction ConditionsOperation in experiment
96% With pyridine; dmap; at 20℃; for 6h; D-glucose (900 mg, 5 mmo 1),DMAP (244 mg, 2 mmol) was dissolved in anhydrous pyridine (30 mL)Benzoyl chloride (5 mL) was added,Room temperature reaction for 6 hours.After the reaction is complete,To the reaction solution was added dilute hydrochloric acid (100 ml)Ethyl acetate (30 ml X)Combine organic phase,Saturated brine (30 ml X 2)Anhydrous Na2S04 dry, concentrated,(PE: EpsilonAlpha = 3: 1)To give a white solid (3.36 g, 96%) as shown in formula (A-1).
89% With pyridine; at 0 - 20℃; for 2.16667h; 2,3,4,6-Tetra-O-benzoyl-a-D-glucopyranosyl Benzoate (2) Benzoyl chloride (4.68 g, 33.3 mmol) was added dropwise to a solution of a-D-glucose (1.0 g, 5.6 mmol) in pyridine (30 mL) at 0C. After 10 min at 0C, the solution was stirred for 2 hrs at room temperature. The reaction was quenched by addition of cold water (50 mL) and the product extracted with EtOAc (3 x 50 ml). The combined organic layers were washed with 1 N HCI (3 x 50 mL) followed by brine (50 mL) and then dried, filtered and concentrated. The crude product was purified by recrystallisation with hot Hexane: EtOAc 2:1 to give the title compound as a white solid (3.48 g, 89%). Rf = 0.28 (Hex: EtOAc 8:2). deltaEta (CDCI3, 400 MHz): 8.16 (2H, d, J = 8.0 Hz, H-Ar), 8.02 (2H, d, J = 8.0 Hz, H-Ar), 7.94 (2H, d, J = 8.0 Hz, H-Ar), 7.88 (4H, d, J = 8.0 Hz, H-Ar), 7.66 (1 H, t, J = 8.0 Hz, H-Ar), 7.53-7.28 (14H, m, H-Ar), 6.85 (1 H, d, J = 4.0 Hz, H-1 ), 6.32 (1 H, t, J = 8.0 Hz, H-3), 5.85 (1 H, t, J = 8.0 Hz, H-4), 5.68 (1 H, dd, J = 4.0, 8.0 Hz, H-2), 4.62 (2H, m, H-6a/H-5), 4.59 (1 H, dd, J = 4.0 Hz, J = 12.0 Hz, H-6b) 5C (CDCI3, 100 MHz): 166.1 , 165.9, 165.3, 165.1 , 164.4 (C=0), [133.9, 133.5, 133.4, 133.3, 133.1 130.0, 129.9 (x2), 129.8 (x2), 129.6, 129.0, 128.9, 128.8, 128.6, 128.4 (x3), 128.37 ArC)], 90.0 (C-1 ), 76.6 (C-3), 70.5 (C-2), 70.5 (C-5), 68.9 (C-4), 62.5 (C-6)
63% With pyridine; dmap; at 0 - 20℃; for 16h;Inert atmosphere; BzCl (3.9 mL, 33.3 mmol) was added dropwise with stirring to D-glucose (1.0 g, 5.6 mmol) and DMAP(136 mg, 1.11 mmol) in pyridine (28 mL) at 0 C and the mixture was allowed to warm to roomtemperature. After 16 h, cold H2O (50 mL) was added and the mixture extracted with EtOAc (2 × 100mL). The combined organic layers were washed with aqueous HCl (1.0 M; 2 × 100 mL), brine (50 mL),and dried (MgSO4) and rotary evaporated to give the crude product. Recrystallization from EtOAc andhexanes gave the pentabenzoate 40 (2.46 g, 63%) as a white solid
  • 3
  • [ 492-62-6 ]
  • [ 108-24-7 ]
  • [ 604-68-2 ]
YieldReaction ConditionsOperation in experiment
97.1% With 4-methyl-morpholine; dmap; In dichloromethane; at 0 - 5℃; for 2h; Take 1L three-port reaction bottle, install mechanical stirring, thermometer and constant pressure dropping funnel;200 ml of dichloromethane, 50 g (0.2775 mol) of d-glucose, 140.2 g (1.3875 mol) of N-methylmorpholine, 3.4 g (0.0275 mol) of DMAP were added to dissolve until dissolved; the temperature was lowered to 0-5 C, and 141.6 was slowly added. g (1.3875 mol) acetic anhydride, continue to react for 2 hours after completion; The solvent was distilled off at a high temperature, and 400 g of water was added to the reaction flask after completion, and the solid was stirred and precipitated, washed by filtration, and dried under vacuum to obtain 105.2 g of pentaacetylglucose, the yield was 97.1%;
92% With pyridine; dmap; at 0 - 20℃; for 20h; To (2S, 3R,4S, 5S, 6R)-6-(hyd roxymethyl)tetrahydro-2H-pyran-2, 3,4, 5-tetraol 1 (50 g, 277.7 mmol) in pyridine (500 mL) at 0 C was added DMAP (339 mg, 2.777 mmol) and acetic anhydride (500 mL). The reaction mixture was further stirred at room temperature for 20 h. After completion of the reaction, the pyridine was evaporated under reducedpressure and the residue was diluted with water and extracted with CH2CI2 (thrice). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude compound was purified by trituration with n-hexane to afford 100 g (92% yield) of compound 2 as off white solid.ELSD-Condition-1: [M-?-H] = 408.00; R = 2.88 mm1H NMR (400 MHz, CDCI3) 6: 6.33 (d, J = 3.91 Hz, I H), 5.47 (t, J = 10.03 Hz, I H), 5.07-5.17 (m, 2 H), 4.24-4.29 (m, I H), 4.08-4.15 (m, 2 H), 2.18 (5, 3 H), 2.09 (5, 3 H), 2.04 (5, 3 H), 2.03 (5, 3 H), 2.02 (5, 3 H).
  • 4
  • [ 492-62-6 ]
  • [ 57-55-6 ]
YieldReaction ConditionsOperation in experiment
15.45% With potassium molybdate(VI); 5 wt% ruthenium/carbon; hydrogen; In water; at 220℃; under 62256.2 Torr; for 2h;Sealed tube; A feed comprising 20% dextrose by weight in water was reacted in a high throughput screening batch reactor. The catalytic reaction conditions were carried out in sealed hydrogenolysis reactors at 220 degrees Celsius, at 8.3 MPa (1200 psi) hydrogen pressure for a 2 hour hold period. Products of the reaction were analyzed by gas chromatography (?GC?), which showed lower ethylene glycol selectivity with greater selectivity for propylene glycol using co-catalysts comprising Mo, in the form of potassium molybdate (K2M0O4) with 5% Ru CP, as compared to sodium tungstate (Na2W04) with 5% Ru CP (with the exception of 5K2M0O4 versus 5Na2W04 and I OK2M0O4 versus l0Na2WO4 as to PG selectivity). [58] The GC results also show lower ethylene glycol selectivity with greater selectivity for propylene glycol using co-catalysts comprising Mo, in the form of potassium molybdate (K2M0O4) with 5% Ru CP as compared to ammonium metavanadate (NH4VO3) with 5% Ru CP. [59] Results using various reactor co-catalysts are shown in Table 7-9 below, with 100% dextrose conversion, and without glycerol detected for the runs shown in Tables 7-9.
  • 5
  • [ 492-62-6 ]
  • [ 110-13-4 ]
YieldReaction ConditionsOperation in experiment
65% With hydrogenchloride; 5%-palladium/activated carbon; hydrogen; In chloroform; water; at 100℃; under 45004.5 Torr; for 2h; Willow, pine, mulberry, birch, newspaper, cotton, cotton, cotton, etc. are pulverized and dried. 20 g is added to a 4 L reactor, 2 g of 5% Pd/C is added, 0.4 L of 36% aqueous hydrochloric acid and 1.2 are added. L-chloroform was charged with 6 MPa of hydrogen and reacted at 100 C for 2 hours.Table 1 Preparation of 2,5-hexanedione from different raw materials
  • 6
  • [ 492-62-6 ]
  • [ 4300-97-4 ]
  • C31H47Cl5O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.5% With pyridine; dmap; In dichloromethane; at 0 - 20℃; for 20.5h;Inert atmosphere; D-glucose (XII-1, 5 g, 27.8 mmol) was suspended in anhydrous dichloromethane (80 mL) under nitrogen and the mixture was stirred at room temperature for 5 min then cooled to 0 C and stirred for 10 min. Then, to the resulting mixture, pyridine (30 mL) was added dropwise with stirring for about 10-15 minutes, and N,N-dimethylaminopyridine (0.25 g, 2.04 mmol) was added. The temperature was lowered to 0 C, and a dichloromethane solution of monochloropivaloyl chloride (monochloropivaloyl chloride (XII-2, 23.6 g, 152.9 mmol) dissolved in 15 mL of dichloromethane) was slowly added dropwise to the reaction mixture. Add the time for 30 minutes. After the dropwise addition was completed, the ice bath was removed, and the resulting mixture was stirred at room temperature for 20 hours. The resulting mixture was then poured into dichloromethane (100 mL) and hydrochloric acid (1.5 M,In the resulting mixture of 75 mL), the resulting two phases were separated. The organic layer was washed with sodium bicarbonate solution (100 mL) and organic layer reducedConcentrate to near dryness. Ethanol (95%, 50 mL) was added to the obtained residue, and the mixture was heated to reflux. returnThe flow was kept for 1 hour, and the temperature was gradually lowered (the cooling time was about 30 minutes) to 0 C, and the crystallization was stirred for 2 hours. Filtered, 95%The filter cake was washed with ethanol and dried under vacuum at room temperature overnight to give the desired product intermediate XII-3; i.e., 1,2,3,4,6-O-pentachloropivaloyl-D-glucopyranose. Yield 87.5%;
  • 7
  • [ 492-62-6 ]
  • [ 50547-79-0 ]
  • 1,2,3,4,6-O-pentakis(3-chloro-2,2-dichloromethylpropanoyl)-α-D-glucopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With pyridine; dmap; In dichloromethane; at 0 - 20℃; for 20.5h;Inert atmosphere; D-glucose (XII-1, 28.0 mmol) was suspended in anhydrous dichloromethane (80 mL) under nitrogen and the mixture was stirred at room temperature for 5 min then cooled to 0 C and stirred for 10 min.Then, to the resulting mixture, pyridine (30 mL) was added dropwise with stirring for about 10-15 minutes, and N,N-dimethylaminopyridine (2.04 mmol) was added.The temperature was lowered to 0 C, and a solution of 3-chloro-2,2-dichloromethylpropionyl chloride (XII-11) in dichloromethane was slowly added dropwise to the reaction solution.(Acyl chloride 152.9 mmol was dissolved in 15 mL of dichloromethane) and added dropwise for 30 minutes.After the dropwise addition was completed, the ice bath was removed, and the resulting mixture was stirred at room temperature for 20 hours.Then, the resulting mixture was poured into a mixed solution of dichloromethane (100 mL) and hydrochloric acid (1.5 M, 75 mL), and the obtained two phases were separated.The organic layer was washed with aq. sodium bicarbonate (100 mL).Ethanol (95%, 50 mL) was added to the obtained residue, and the mixture was heated to reflux. The mixture was refluxed for 1 hour, and the temperature was gradually lowered (the cooling time was about 30 minutes) to 0 C, and the crystallization was stirred for 2 hours.Filtration, washing the filter cake with 95% ethanol, and drying under vacuum at room temperature overnight to obtain the target product intermediate XII-12;1,2,3,4,6-O-penta(3-chloro-2,2-dichloromethylpropanoyl)-D-glucopyranose. Yield 88%;
  • 8
  • [ 492-62-6 ]
  • [ 4301-04-6 ]
  • 1,2,3,4,6-O-pentakis(2,2-dichloromethylpropanoyl)-α-D-glucopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.3% With pyridine; dmap; In dichloromethane; at 0 - 20℃; for 20.5h;Inert atmosphere; D-glucose (XII-1, 5 g, 27.8 mmol) was suspended in anhydrous dichloromethane (80 mL) under nitrogen and the mixture was stirred at room temperature for 5 min then cooled to 0 C and stirred for 10 min.Then, pyridine (30 mL) was added dropwise to the resulting mixture over about 10-15 minutes with stirring, and N,N-dimethylaminopyridine (0.25 g, 2.04 mmol) was added.The temperature was lowered to 0 C, and a solution of 2,2-dichloromethylpropionyl chloride (XII-7) in dichloromethane (23.6 g of acid chloride (152.9 mmol) dissolved in 15 mL of dichloromethane) was slowly added dropwise to the reaction solution. Add 30 minutes.After the dropwise addition was completed, the ice bath was removed, and the resulting mixture was stirred at room temperature for 20 hours.The resulting mixture was then poured into dichloromethane (100 mL) and hydrochloric acid (1.5 M, 75 mL).In the resulting mixture, the resulting two phases were separated.The organic layer was washed with aq. sodium bicarbonate (100 mL).Ethanol (95%, 50 mL) was added to the obtained residue, and the mixture was heated to reflux.The mixture was refluxed for 1 hour, and the temperature was slowly lowered to 0 C (the cooling time was about 30 minutes), and the crystallization was stirred for 2 hours.Filtration, washing the filter cake with 95% ethanol, and drying under vacuum at room temperature overnight to obtain the desired product intermediate XII-8; that is, 1,2,3,4,6-O-penta(2,2-dichloromethylpropanoyl) -D-glucopyranose. Yield 88.3%;
  • 9
  • [ 492-62-6 ]
  • [ 77-76-9 ]
  • [ 160651-67-2 ]
YieldReaction ConditionsOperation in experiment
82% With sulfuric acid; In acetone; at 20℃; for 1.5h; glucose (1.8 g, 10 mmol) dissolved in 20 ml of acetone, then adding 1, 1 - dimethoxy propane (2.1 g, 20 mmol) and sulfuric acid (1 drop), stirring at room temperature for 1 hour, concentrated to do, ethyl acetate to dissolve the residue, in order to water washing, drying of the organic layer concentrated, to obtain 2 . 13 g colorless oil of, yield 82%.
  • 10
  • [ 492-62-6 ]
  • [ 108-24-7 ]
  • [ 4163-60-4 ]
YieldReaction ConditionsOperation in experiment
92.5% With sodium acetate; at 100 - 130℃; under 760.051 Torr; for 4h;Large scale; acetic anhydride 2000 kg,Sodium acetate 40kg added to 5000L jacketed reactor,Then add 616 kg of glucose twice,Atmospheric pressure 100 ~ 130 insulation 4h,After completion of the reaction, the mixture was distilled under reduced pressure at 95 C / -0.080 MPa,Recycle acetic acid and acetic anhydride.After cooling, the ethanol was added to the concentrated product, and the material was introduced into the crystallization kettle. The mother liquor was introduced into the beta-pentaacetylglucose seed crystal and the cooling rate was controlled. The crystals were crystallized at 10 to 35 C for 24 h and centrifuged. The filter cake was washed with deionized water Twice after drying 12h, get beta-pentaacetyl glucose, the yield of 92.5%. The mother liquor is distilled to recover ethanol.
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