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[ CAS No. 617-55-0 ] {[proInfo.proName]}

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Chemical Structure| 617-55-0
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Product Details of [ 617-55-0 ]

CAS No. :617-55-0 MDL No. :MFCD00066215
Formula : C6H10O5 Boiling Point : -
Linear Structure Formula :- InChI Key :YSEKNCXYRGKTBJ-BYPYZUCNSA-N
M.W : 162.14 Pubchem ID :10285815
Synonyms :

Calculated chemistry of [ 617-55-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.69
TPSA : 72.83 Ų

Pharmacokinetics

GI absorption : High
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) : -7.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : -0.68
Log Po/w (WLOGP) : -0.92
Log Po/w (MLOGP) : -0.58
Log Po/w (SILICOS-IT) : -0.29
Consensus Log Po/w : -0.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.09
Solubility : 133.0 mg/ml ; 0.819 mol/l
Class : Very soluble
Log S (Ali) : -0.37
Solubility : 68.4 mg/ml ; 0.422 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.1
Solubility : 204.0 mg/ml ; 1.26 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 617-55-0 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P210-P280-P305+P351+P338+P310-P333+P313-P403+P235 UN#:2924
Hazard Statements:H225-H317-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 617-55-0 ]

* 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 [ 617-55-0 ]
  • Downstream synthetic route of [ 617-55-0 ]

[ 617-55-0 ] Synthesis Path-Upstream   1~29

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YieldReaction ConditionsOperation in experiment
98% at 25℃; Cooling with ice Thionyl chloride (117 g, 0.98 mol) was added to the solution of L-malic acid (59.9 g, 0.45 mol) in methanol (400 mL) in ice-water bath. The resulting reaction mixture was stirred overnight at room temperature (rt, 25 °C) after the completion of the addition. The reaction was monitored with TLC (EtOAc:MeOH =10:1). The solvent was removed in vacuo. Saturated NaHCO3 solution (200 mL) was added, and the aqueous phase extracted with EtOAc (3 × 150 mL). The combined organic phases were washed successively with water (3 × 80 mL), brine (3 × 80 mL) and dried over Na2SO4, and the solvent was removed under reduced pressure. The ester 2 was isolated as light yellow oil in 98percent yield (71.5 g, 0.44 mol).
94%
Stage #1: for 0.166667 h;
Stage #2: at 20℃;
To a 2 L flask charged with stir bar andanhydrous methanol (500 mL) was added acetyl chloride (22.4 mL, 315 mmol, 0.6equiv) dropwise. The resultant solution was stirred for 10 min at rt, then (S)-malic acid(70.55 g, 526 mmol) was added. The reaction was stirred overnight at rt, thenconcentrated in vacuo. Silica gel chromatography (96:4 CH2Cl2/MeOH) afforded the titlecompound as a pale yellow oil (80.57 g, 94percent), with spectroscopic data in agreementwith literature values.15
80%
Stage #1: at 20℃; for 0.166667 h; Inert atmosphere
Stage #2: at 20℃; for 18 h; Inert atmosphere
Acetyl chloride (8.21 mL, 116 mmol) was added to methanol (150 mL) at room temperature followed after 10 min by (S)-malic acid (25 g, 186 mmol). The solution was stirred at room temperature for 18 h before the volatile components were evaporated under reduced pressure. The resultant residue was purified by flash column chromatography using CH2Cl2/MeOH (95:5) as eluent to afford the title compound 23 (22.67 g, 80percent) as a yellow oil. The spectroscopic data was in agreement with those reported in the literature.24 Rf (5percent MeOH/CH2Cl2) 0.51; [α]D20 +1.6 (c 0.80 in CHCl3); lit.24 [α]D25 +3.1 (c in 0.80, CHCl3); δH (300 MHz; CDCl3; Me4Si) 2.72 (2H, dd, J 16.4, 4.4 Hz, H-3), 3.35 (1H, br s, OH), 3.61 (3H, s, C-4OMe), 3.67 (3H, s, C-1OMe), 4.42 (1H, dd, J 6.3, 4.4 Hz, H-2); δC (75 MHz; CDCl3; Me4Si) 38.4 (CH2, C-3), 51.9 (CH3, C-4OMe), 51.6 (CH3, C-1OMe), 67.2 (CH, C-2) 170.9 (CO, C-4), 173.6 (CO, C-1).
67.2% for 3 h; Reflux In a reaction vessel23.6 g (0.2 mol)L-malic acid,And methanol was added40 ml,To dissolve,Concentrated sulfuric acid was then added4ml,After heating under reflux for 3 hours,Cooled to room temperature,The reaction solution was poured into water,Fully stirred,The residue was diluted with dichloromethane (50 ml * 3)extraction,The organic phases were combined,Washed,Dried over anhydrous sodium sulfate,stress reliever,After recovery of the solvent by distillation,To give dimethyl L-malate as a white solid18.8 g,Yield64.8percent.

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[5] Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7227 - 7237
[6] Archiv der Pharmazie, 1982, vol. 315, # 3, p. 262 - 273
  • 5
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Reference: [1] Tetrahedron, 2015, vol. 71, # 33, p. 5362 - 5370
  • 6
  • [ 67-56-1 ]
  • [ 28127-65-3 ]
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  • 7
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  • 8
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[2] Patent: EP367895, 1990, A1,
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  • 10
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  • 13
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  • 23
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  • 24
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YieldReaction ConditionsOperation in experiment
97.9 - 98.8 % ee With hydrogen In Dimethyl ether at 56 - 110℃; for 0.5 - 2 h; HYDROGENATION OF DIMETHYL MALATE:; The following conditions were used Hydrogen pressure 0,1, 10 and 30 bar Substrate 0,4 and 1,5 molpercent Catalyst CuMn AI203, particle size 90-180 um Samples are taken at regular intervals after the substrate feed is started. Experiment 1: This was performed according to the procedure described above in Materials, Equipment and Activation Procedure. The reaction temperature was 56°C, Hydrogen pressure was 10bar, DME pressure was 150bar, substrate concentration in solution was 0.4 molpercent, and 10G of catalyst were used. The following results were obtained: Time on DM L DE BT HGB H-THF HGB equiv Selectivity stream areapercent areapercent 5 67.5 0.22 15.16 0.14 15.86 0.1 31.02 95.4percent 13 58.4 0.09 21.45 0.27 18.29 0.07 39.74 95.5percent 20 63.1 0.15 19.8 0.37 15.6 0.07 35.4 95.9percent 30 67.8 0.07 18.2 0.58 12.39 0.06 30.59 95.0percent 60 76.5 0.04 15 0.48 7.22 0.04 22.22 94.6percent DM = dimethyl malate L = 2 (5H)-Furanone DE = 3,4-dihydroxy methyl butyrate ester BT = butanetriol HGB = 3-hydroxy-gammabutyrolactone (produced by in-situ cyclisation of 3,4-dihydroxy methyl butyrate ester) H-THF = hydroxy-THF Notes: HGB EQUIVALENT = areapercent"HGB"+ areapercent"Dihydroxy ester" (as hydroxy ester can be cyclise to HGB) SELECTIVITY DEFINED AS (AREApercent USEFUL PRODUCTS) / (AREA percent OF ALL PRODUCTS) HGB (S) was obtained in 97.9percent ee Experiment 2: This was performed according to the procedure described above in Materials, Equipment and Activation Procedure. The reaction temperature was 110°C, Hydrogen pressure was 10bar, DME pressure was 150bar, substrate concentration in solution was 1.5 molpercent, and 5.9g of catalyst were used. The following results were obtained : Time on DM L DE BT HGB H-THF HGB equiv Selectivity stream areapercent areapercent 5 64.1 0.55 18.22 1.6 15.3 33.52 93.4percent 15 72.6 0.24 15.38 0.9 10 0.1 25.38 92.6percent 30 77.6 0.16 13.3 0.5 7.8 0.1 21.1 94.2percent Note: HGB (S) obtained in 98.8percent ee Conclusion: These experiments illustrate high selectivity for HGB in the hydrogenation of dimethyl malate EXPERIMENT-MEOH removal and the effect on the conversion of LDMM to HGB Experiment 3: This was performed according to the procedure described above in Materials, Equipment and Activation Procedure. The reaction temperature was 80°C, Hydrogen pressure was 10bar, DME pressure was 150bar, substrate concentration in solution was 0.4 molpercent, and 87g of catalyst were used. After 2 hours on stream, the product was found to contain 39.8 areapercent starting material and 51.5 areapercent HGB-EQUIVALENT (as defined in Example 1). The product was formed with 85.5percent selectivity. The collected product from this experiment, after depressurisation and removal of Methanol, was used as the feed for another hydrogenation, under otherwise identical conditions. The following results were obtained. Time on DM areapercent L DE BT HGB HGB Selectivity stream equiv areapercent 50 14.7 5.3 15.2 8 47.4 62.6 73.4percent 60 18. 8 4.4 14. 8 11.7 45.5 60.3 74.3percent 75 21.15 3.7 21.1 11.5 43.2 64. 3 81.5percent 90 13. 4 7. 1 5.5 59.1 66.2 76.4percent 105 26.7 3.4 17.5 8.7 40.6 58. 1 79.3percent 120 25.6 2.3 17.7 9.5 42 59.7 80. 2percent Conclusions : When the reaction products from one incomplete hydrogenation are depressurised and Methanol removed by evaporation, then re-hydrogenated the conversion is increased FROM-50percent TO-60percent, and the selectivity remains approximately constant.
Reference: [1] Patent: WO2005/23737, 2005, A1, . Location in patent: Page/Page column 10-12
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Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 11, p. 1215 - 1218
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Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 11, p. 1215 - 1218
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