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[ CAS No. 54664-61-8 ]

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Chemical Structure| 54664-61-8
Chemical Structure| 54664-61-8
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CAS No. :54664-61-8 MDL No. :MFCD03002563
Formula : C9H12O4 Boiling Point : 227.098°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :184.19 g/mol Pubchem ID :10192610
Synonyms :

Safety of [ 54664-61-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54664-61-8 ]

  • Downstream synthetic route of [ 54664-61-8 ]

[ 54664-61-8 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 79-24-3 ]
  • [ 54664-61-8 ]
  • Acetic acid (3aR,4S,6R,6aR)-6-acetoxy-3-methyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazol-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With potassium carbonate; p-toluenesulfonyl chloride In toluene at 60 - 65℃; for 6h;
  • 2
  • [ 108-05-4 ]
  • [ 29783-26-4 ]
  • [ 54664-61-8 ]
  • [ 60176-77-4 ]
YieldReaction ConditionsOperation in experiment
1: 78% 2: 10% With triethylamine In tetrahydrofuran for 4h; Ambient temperature; lipase from Mucor sp.;
1: 72% 2: 22% With Chirazyme In acetic acid butyl ester for 12h;
1: 65% 2: 32% With triethylamine In tetrahydrofuran for 2.5h; Ambient temperature; pancreatin;
1: 65% 2: 32% With triethylamine In tetrahydrofuran for 2.5h; Ambient temperature; pancreatin; variations of concentrations, time; other vinyl alkanoate;
1: 64% 2: 28% With Chirazyme In various solvent(s) at 4℃; for 4.75h;
1: 64% 2: 28% With Chirazyme In various solvent(s) at 4℃; for 4.75h; also isopropenyl acetate as acyl donor; var. solvents, temp. and time; var. concentration of reagents; effect of various additives;
61% With Novozym 435 In various solvent(s) at 20℃; for 3h;
1: 60.31% 2: 1.27% With Pancreatin In tetrahydrofuran; water for 8 - 48h; It has been found that the enzyme preparations vary lot to lot, leading to differences in the rate of acetylation as well as selectivity. The water content of the enzyme is a major causative factor in the variability as shown in Table 1. TABLE 1 % water wt/wt monoacetate pancreatin time diol monoacetate diacetate enantiomer 3.0% 8 hrs 3.24% 60.31% 34.76% 1.68% 6.6% 23 hrs 2.41% 76.74% 19.65% 1.27% 12% 48 hrs 4% 79.1% 16.9% not determined Optimum results are obtained with a water content of 5-7%. Larger amounts of water decrease the rate of the reaction and do not provide an improvement in selectivity between the mono-acetate and the di-acetate when a reasonable reaction endpoint (<5% diol) is obtained. With low water content, the reaction rate is greatly accelerated and the selectivity between the mono-acetate and the di-acetate decreases.Another factor, which influences selectivity of the transesterification, is the concentration of the reaction. It has been found that the amount of diacetate formed increases as the dilution increases. Thus, at 0.2 molar concentration of the dihydroxycyclopentene, the ratio of monoacetate to diacetate product is 1 to 1, at 1 molar it is 3.3:2, and at 2 molar it is 3.6 to 2.Other factors which influences the transesterification include the temperature of the reaction, use of pancreatin or lipase and the addition of varying amounts of triethylamine as shown in Table 2. Optimum conditions for the transesterification are the use of pancreatin at 5° C. with added triethylamine at a concentration of 2 molar of dihydroxycyclopentene. Results listed in Table 2 are from reactions conducted using the conditions described in the EXAMPLE. TABLE 2 Proportion of Reaction Mono- Di- Time Conditions acetate acetate Diol % ee elapsed Lipase 100 63 0 91.5 24 20° C. 40° C. 100 100 0 85.4 24 Lipase 10° C. 100 36 0 86.3 24 Lipase 0° C. Lipase 100 20 74 82.3 22 100 20 0 100 20 51 85 26 100 20 0 100 22 11 92.8 48 100 22 0 10° C. 100 27 27 85.4 22 Lipase 100 28 15 88.9 26 100 28 0 100 32 0 94.02 485%, Et3N, 100 50 7 87.8 16 20° C. 100 50 0 Lipase 100 55 0 92.9 235%, Et3N, 100 26 13 90.4 23 5° C., Lipase 100 25 0 100 28 5 93.9 30 100 28 025%, Et3N, 100 25 36 82.9 16 5° C., Lipase 100 25 0 100 26 16 88.8 22 100 27 0 100 32 0 97.7 40 pancreatin 100 48 0 92.1 23 20° C. pancreatin 100 20 21 90.9 22 5° C. pancreatin 100 23 0 96.2 22 5° C., 5%Et3N e.e. = % major isomer - % minor isomer
1: 53% 2: 43% With triethylamine In tetrahydrofuran at 20℃; for 24h; Enzymatic reaction; enantioselective reaction; Procedure for the enzymatic desymmetrization of the cis-diol 2a To a stirred solution of the diol 2a (0.200 g, 1.998 mmol), vinyl acetate (1.33 mL, 13.983 mmol) and triethylamine (1.95 mL, 13.983 mmol) in dry THF (5 mL) was added Pancreatin (1.000 g, 5 wt equiv, Sigma 4USP). Thesuspension was stirred for 24 h at room temperature and then filtered over apad of Celite. The solid was washed with ethyl acetate (50 mL) and the filtrate was concentrated. The oily residue was then chromatographed on silica gel (cyclohexane/ethyl acetate 4:1 to 2:1) to yield the monoacetate (-)-2f as ayellow solid (0.150 g, 1.059 mmol, 53%) and the diacetate derivative 4f asyellow oil (0.160 g, 1.125 mmol, 43%). (-)-2f: 1H NMR: (300 MHz, CDCl3) d (ppm): 6.14-6.09 (1H, m, H2), 6.01-5.96(1H, m, H3), 5.54-5.45 (1H, m, H1), 4.75-4.68 (1H, m, H4), 2.80 (1H, dt, J = 14.7,7.4 Hz, H5), 2.05 (3H, s, Ac), 1.66 (1H, dt, J = 14.7, 3.8 Hz, H5). 13C NMR:(75 MHz, CDCl3) d (ppm):170.9 (CO Ac), 138.6 (C2), 132.6 (C3), 77.2 (C1), 74.9(C4), 40.6 (C5), 21.3 (Ac). [a]D20 70.3 (c 1, CHCl3); 99.9 ee determined by GCmeasurement on the crude product (Lipodex E, 25 m 0.25 mm).
82.9 - 97.7 % ee With lipase In tetrahydrofuran; water at 5 - 20℃; for 16 - 40h; Other factors which influences the transesterification include the temperature of the reaction, use of pancreatin or lipase and the addition of varying amounts of triethylamine as shown in Table 2. Optimum conditions for the transesterification are the use of pancreatin at 5° C. with added triethylamine at a concentration of 2 molar of dihydroxycyclopentene. Results listed in Table 2 are from reactions conducted using the conditions described in the EXAMPLE. TABLE 2 Proportion of Reaction Mono- Di- Time Conditions acetate acetate Diol % ee elapsed Lipase 100 63 0 91.5 24 20° C. 40° C. 100 100 0 85.4 24 Lipase 10° C. 100 36 0 86.3 24 Lipase 0° C. Lipase 100 20 74 82.3 22 100 20 0 100 20 51 85 26 100 20 0 100 22 11 92.8 48 100 22 0 10° C. 100 27 27 85.4 22 Lipase 100 28 15 88.9 26 100 28 0 100 32 0 94.02 485%, Et3N, 100 50 7 87.8 16 20° C. 100 50 0 Lipase 100 55 0 92.9 235%, Et3N, 100 26 13 90.4 23 5° C., Lipase 100 25 0 100 28 5 93.9 30 100 28 025%, Et3N, 100 25 36 82.9 16 5° C., Lipase 100 25 0 100 26 16 88.8 22 100 27 0 100 32 0 97.7 40 pancreatin 100 48 0 92.1 23 20° C. pancreatin 100 20 21 90.9 22 5° C. pancreatin 100 23 0 96.2 22 5° C., 5%Et3N e.e. = % major isomer - % minor isomer
82.3 - 94.02 % ee With lipase In tetrahydrofuran; water at 0 - 40℃; for 22 - 48h; Other factors which influences the transesterification include the temperature of the reaction, use of pancreatin or lipase and the addition of varying amounts of triethylamine as shown in Table 2. Optimum conditions for the transesterification are the use of pancreatin at 5° C. with added triethylamine at a concentration of 2 molar of dihydroxycyclopentene. Results listed in Table 2 are from reactions conducted using the conditions described in the EXAMPLE. TABLE 2 Proportion of Reaction Mono- Di- Time Conditions acetate acetate Diol % ee elapsed Lipase 100 63 0 91.5 24 20° C. 40° C. 100 100 0 85.4 24 Lipase 10° C. 100 36 0 86.3 24 Lipase 0° C. Lipase 100 20 74 82.3 22 100 20 0 100 20 51 85 26 100 20 0 100 22 11 92.8 48 100 22 0 10° C. 100 27 27 85.4 22 Lipase 100 28 15 88.9 26 100 28 0 100 32 0 94.02 485%, Et3N, 100 50 7 87.8 16 20° C. 100 50 0 Lipase 100 55 0 92.9 235%, Et3N, 100 26 13 90.4 23 5° C., Lipase 100 25 0 100 28 5 93.9 30 100 28 025%, Et3N, 100 25 36 82.9 16 5° C., Lipase 100 25 0 100 26 16 88.8 22 100 27 0 100 32 0 97.7 40 pancreatin 100 48 0 92.1 23 20° C. pancreatin 100 20 21 90.9 22 5° C. pancreatin 100 23 0 96.2 22 5° C., 5%Et3N e.e. = % major isomer - % minor isomer
90.9 - 92.1 % ee With Pancreatin In tetrahydrofuran; water at 5 - 20℃; for 22 - 23h; Other factors which influences the transesterification include the temperature of the reaction, use of pancreatin or lipase and the addition of varying amounts of triethylamine as shown in Table 2. Optimum conditions for the transesterification are the use of pancreatin at 5° C. with added triethylamine at a concentration of 2 molar of dihydroxycyclopentene. Results listed in Table 2 are from reactions conducted using the conditions described in the EXAMPLE. TABLE 2 Proportion of Reaction Mono- Di- Time Conditions acetate acetate Diol % ee elapsed Lipase 100 63 0 91.5 24 20° C. 40° C. 100 100 0 85.4 24 Lipase 10° C. 100 36 0 86.3 24 Lipase 0° C. Lipase 100 20 74 82.3 22 100 20 0 100 20 51 85 26 100 20 0 100 22 11 92.8 48 100 22 0 10° C. 100 27 27 85.4 22 Lipase 100 28 15 88.9 26 100 28 0 100 32 0 94.02 485%, Et3N, 100 50 7 87.8 16 20° C. 100 50 0 Lipase 100 55 0 92.9 235%, Et3N, 100 26 13 90.4 23 5° C., Lipase 100 25 0 100 28 5 93.9 30 100 28 025%, Et3N, 100 25 36 82.9 16 5° C., Lipase 100 25 0 100 26 16 88.8 22 100 27 0 100 32 0 97.7 40 pancreatin 100 48 0 92.1 23 20° C. pancreatin 100 20 21 90.9 22 5° C. pancreatin 100 23 0 96.2 22 5° C., 5%Et3N e.e. = % major isomer - % minor isomer

Reference: [1]Theil, Fritz; Schick, Hans; Weichert, Dieter; Tannenberger, Klaus; Klappach, Guenther [Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 3, p. 497 - 499]
[2]Ghorpade, Sandeep R.; Kharul, Rajendra K.; Joshi, Rohini R.; Kalkote, Uttam R.; Ravindranathan [Tetrahedron Asymmetry, 1999, vol. 10, # 5, p. 891 - 899]
[3]Theil, Fritz; Schick, Hans; Lapitskaya, Margarita A.; Pivnitsky, Kasimir K. [Liebigs Annalen der Chemie, 1991, # 3, p. 195 - 200]
[4]Theil, Fritz; Schick, Hans; Lapitskaya, Margarita A.; Pivnitsky, Kasimir K. [Liebigs Annalen der Chemie, 1991, # 3, p. 195 - 200]
[5]Ghorpade, Sandeep R.; Kharul, Rajendra K.; Joshi, Rohini R.; Kalkote, Uttam R.; Ravindranathan [Tetrahedron Asymmetry, 1999, vol. 10, # 5, p. 891 - 899]
[6]Ghorpade, Sandeep R.; Kharul, Rajendra K.; Joshi, Rohini R.; Kalkote, Uttam R.; Ravindranathan [Tetrahedron Asymmetry, 1999, vol. 10, # 5, p. 891 - 899]
[7]Saul, Simon; Corr, Stuart; Micklefield, Jason [Angewandte Chemie - International Edition, 2004, vol. 43, # 41, p. 5519 - 5523]
[8]Current Patent Assignee: PFIZER INC - US6974834, 2005, B2 Location in patent: Page/Page column 4-5
[9]Specklin, Simon; Dikova, Anna; Blanc, Aurélien; Weibel, Jean-Marc; Pale, Patrick [Tetrahedron Letters, 2014, vol. 55, # 51, p. 6987 - 6991]
[10]Current Patent Assignee: PFIZER INC - US6974834, 2005, B2 Location in patent: Page/Page column 4-5
[11]Current Patent Assignee: PFIZER INC - US6974834, 2005, B2 Location in patent: Page/Page column 4-5
[12]Current Patent Assignee: PFIZER INC - US6974834, 2005, B2 Location in patent: Page/Page column 4-5
  • 3
  • [ 54664-61-8 ]
  • [ 79958-77-3 ]
  • [ 111253-23-7 ]
YieldReaction ConditionsOperation in experiment
57.3% With potassium carbonate; p-toluenesulfonyl chloride In toluene at 60 - 65℃; for 6h;
  • 4
  • [ 54664-61-8 ]
  • [ 13154-41-1 ]
  • [ 111253-24-8 ]
YieldReaction ConditionsOperation in experiment
68.4% With potassium carbonate; p-toluenesulfonyl chloride In toluene at 60 - 65℃; for 6h;
  • 5
  • [ 54664-61-8 ]
  • [ 60176-77-4 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide; phosphate buffer at 32℃; for 14h; pH= 7;
74% With sodium hydroxide; sodium phosphate buffer; Trichosporon beigelii (NCIM 3326) In ethanol for 26h;
74% With Trichosporon beigelii NCIM 3326 In ethanol at 20℃; for 26h; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee;
In various solvent(s)
Multi-step reaction with 2 steps 1: 94 percent / K2CO3 / methanol / 4 h / 0 °C 2: 72 percent / Et3N; pancreatin / tetrahydrofuran / 3 h / 20 °C

  • 6
  • [ 54664-61-8 ]
  • [ 60410-16-4 ]
YieldReaction ConditionsOperation in experiment
96% With Novosyme sp 435 lipase In various solvent(s) at 20℃; for 18h;
96% With Novozym 435
96% With lipase from candida antartica In aq. phosphate buffer at 20℃; for 24h; Enzymatic reaction; enantioselective reaction; Procedure for the enzymatic desymmetrization of the cis-diacetate 4f To a stirred solution of the diacetate 4f (0.100 g, 0.543 mmol) in2.7 mL freshly prepared aqueous phosphate buffer solution (0.1 M, pH 8) wasadded Candida antarctica CAL-B (5.4 mg). The suspension was stirred for 24 h atroom temperature and then filtered over a pad of Celite. The solid waswashed with water (10 mL) and then with ethyl acetate (10 mL). The aqueouslayer was extracted with ethyl acetate (4 10 mL). The combined organiclayers were dried over sodium sulfate and concentrated in vacuo. The oilyresidue was then chromatographed on silica gel (cyclohexane/ethyl acetate 4:1to 2:1) to yield the monoacetate (+)-2f as a white solid (0.074 g, 0.521 mmol,96%). Spectral data are identical to those already reported for (-)-2f (see Ref. 16), 98.5 ee determined by GC measurement on the crude product(Lipodex E, 25 m 0.25 mm).
95% With sodium azide; lyophilized electric eel acetyl cholinesterase; sodium dihydrogen phosphate buffer In water at 22℃; for 5h;
94% With acetylcholinesterase
94% With Amano lipase In aq. phosphate buffer at 20℃; for 24h; Schlenk technique; Inert atmosphere; Enzymatic reaction;
93.6% With sodium azide; acetyl cholinesterase at 23℃; for 5.5h; aq. phosphate buffer, pH=6.85;
93% With sodium azide; phosphate buffer; electric eel acetylcholine esterase for 9h;
92% With Candida antarctica lipase B In aq. phosphate buffer at 22℃; for 16h; Enzymatic reaction; enantioselective reaction;
90% With water at 25℃; for 2h; pH 8.0 phosphate buffer, Candida antarctica lipase B (Novo SP-435); other meso-diacetates; enzymatic asymmetrization of meso-2-cycloalken-1,4-diacetates in aqueous media;
90% With water at 25℃; for 2h; pH 0.8 phosphate buffer, Candida antarctica lipase B (Novo SP-435);
89% With acetylcholinesterase
89% With Novozym 435 lipase In aq. phosphate buffer; dichloromethane at 23 - 24℃;
87% With phosphate buffer enzymatic hydrolysis in presence of the different lipases as biocatalysts;
87% With phosphate buffer at 25℃; Pseudomonas cepacia lipase;
87% With sodium azide In aq. phosphate buffer at 20℃; Enzymatic reaction; enantioselective reaction;
85% With acetyl cholinesterase for 12h; pH 7;
85% With sodium hydroxide In acetonitrile at 35℃; for 8h; lipase from Mucor sp., SOERENSEN phosphate buffer pH 6;
85% With sodium azide 5 The synthesis of ligand 28 is depicted in Scheme 3.8. Enantiopure cyclopentenyl alcohol 22 was prepared according to a previously reported procedure. TBS protection and hydrolysis of acetate 22 afforded the alcohol 23 in quantitative yield. It was converted to the corresponding bromo acetal utilizing ethyl vinyl ether and NBS in CH2C12 followed by removal of TBS to give alcohol 24 in 85% yield over two steps. Treatment of alcohol 24 with NaH and propargyl bromide in the presence of TBAI gave the cyclization precursor 25 in 90% yield. The cascade cyclization using tri-w-butyltin hydride in refluxing toluene initiated by AIBN generated the tricyclic alkene 26 in 79% yield. Acetal reduction with trifluoroboron diethyl etherate and triethylsilane provided the alkene 27 in 76% yield.Cleavage of the double bond by ozonolysis at -78 °C followed by NaBH4 reduction at -15 °C in a single operation afforded the P2 ligand 28 in 85% yield.Treatment of alcohol 23 under Mitsunobu condition and the subsequent hydrolysis resulted in the corresponding inverted alcohol 29 in 90% yield over 2 steps.Following the same procedure described earlier, ligand 30 was synthesized.
80% With sodium hydroxide for 48h; Ambient temperature;
80% With electric eel acetylcholine esterase
60% In acetone Ambient temperature; porcine pancreas lipase (steapsin), phosphate buffer (pH 7), 3-5 d;
57% With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; porcine pancreatic lipase In water at 37℃; for 28h; pH 7.0;
With sodium hydroxide; phosphate buffer; Pseudomonas cepacia Lipase PS-30 In acetone
With water Enzymatic reaction;
With novozyme 435 Inert atmosphere; Enzymatic reaction;
With disodium hydrogenphosphate In water at 25 - 30℃; for 14h; Enzymatic reaction; 11 Cis-3,5-diacetoxy-l-cyclopentene (100 g) was added to 0.5M disodium hydrogen phosphate soution of pH 7 (155 g) at 25-30°C. Novozyme-435 immobilized enzyme (0.5 g) was added to the resulting mixture and then stirred for 14 hours. The enzyme was recovered by filtration throgh a buchner funnel to use for next batches. The filtrate was extracted with methylene dichloride (5 x 1000 ml) at 25-30°C. The combined organic layer was dried over anhydrous sodium sulfate, followed by evaporation of the solvent under vacuum at below 40°C. The resulting residue was degassed for 1 hour at 40°C, followed by the addition of diisopropyl ether (300 ml) at 40°C and then stirring the suspension to get a clear solution. The solution was cooled to 0-5°C and then stirred for 30 minutes. The resulting white colored solid was filtered and then dried at 25-30°C under vacuum to produce 50 g of (lS,4R)-cis-4-acetoxy-2-cyclopenten-l-ol [Purity by GC: 99.9%; Chiral Purity: 99.9%; specific optical rotation: +66° (c=2.5%>, CHC13) (Reported Specific optical rotation: +68+/-2°, c = 2.3% , CHCl3)].
With Candida Antartica CAL-B In aq. phosphate buffer at 22℃; for 16h; Inert atmosphere; Enzymatic reaction;

Reference: [1]Tietze, Lutz F.; Stadler, Christian; Böhnke, Niels; Brasche, Gordon; Grube, Alexander [Synlett, 2007, # 3, p. 485 - 487]
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[3]Specklin, Simon; Dikova, Anna; Blanc, Aurélien; Weibel, Jean-Marc; Pale, Patrick [Tetrahedron Letters, 2014, vol. 55, # 51, p. 6987 - 6991]
[4]Jung, Michael E.; Berliner, Judith A.; Angst, Daniela; Yue, Dawei; Koroniak, Lukasz; Watson, Andrew D.; Li, Rongsong [Organic Letters, 2005, vol. 7, # 18, p. 3933 - 3935]
[5]Oppolzer, Wolfgang; Gaudin, Jean-Marc; Birkinshaw, Timothy N. [Tetrahedron Letters, 1988, vol. 29, # 37, p. 4705 - 4708]
[6]Cunha, Ana V.; Havenith, Remco W. A.; Holzheimer, Mira; Minnaard, Adriaan J.; Schouten, Stefan; Sinninghe Damsté, Jaap S. [Angewandte Chemie - International Edition, 2021, vol. 60, # 32, p. 17504 - 17513][Angew. Chem., 2021, vol. 133, p. 17645 - 17654]
[7]Deardorff, Donald R.; Matthews, A. J.; McMeekin, D. Scott; Craney, Chris L. [Tetrahedron Letters, 1986, vol. 27, # 11, p. 1255 - 1256]
[8]Basra, Sanjivanjit K.; Drew, Michael G.B.; Mann, John; Kane, Peter D. [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 21, p. 3592 - 3598]
[9]Delayre, Bastien; Fung, Cédric; Wang, Qian; Zhu, Jieping [Helvetica Chimica Acta, 2021, vol. 104, # 8]
[10]Johnson, Carl R.; Bis, Scott J. [Tetrahedron Letters, 1992, vol. 33, # 48, p. 7287 - 7290]
[11]Johnson, Carl R.; Bis, Scott J. [Tetrahedron Letters, 1992, vol. 33, # 48, p. 7287 - 7290]
[12]Danishefsky, Samuel J.; Cabal, Maria Paz; Chow, Ken [Journal of the American Chemical Society, 1989, vol. 111, # 9, p. 3456 - 3457]
[13]Krout, Michael R.; Henry, Christopher E.; Jensen, Thomas; Wu, Kun-Liang; Virgil, Scott C.; Stoltz, Brian M. [Journal of Organic Chemistry, 2018, vol. 83, # 13, p. 6995 - 7009]
[14]Laumen, Kurt; Schneider, Manfred P. [Journal of the Chemical Society. Chemical communications, 1986, # 16, p. 1298 - 1299]
[15]Siddiqi; Oertel; Chen; Schneller [Journal of the Chemical Society. Chemical communications, 1993, # 8, p. 708 - 709]
[16]Deardorff, Donald R.; Windham, Colin Q.; Craney, Chris L.; Beaudegnies, Renaud; Ghosez, Leon [Organic Syntheses, 1996, vol. 73, p. 25 - 25]
[17]Ghosh, Arun K.; Liu, Wenming [Journal of Organic Chemistry, 1997, vol. 62, # 23, p. 7908 - 7909]
[18]Theil, Fritz; Schick, Hans; Weichert, Dieter; Tannenberger, Klaus; Klappach, Guenther [Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 3, p. 497 - 499]
[19]Current Patent Assignee: KUMAMOTO UNIVERSITY; PURDUE UNIVERSITY SYSTEM - WO2012/31237, 2012, A1 Location in patent: Page/Page column 27; 28
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[26]Schnermann, Martin J.; Beaudry, Christopher M.; Genung, Nathan E.; Canham, Stephen M.; Untiedt, Nicholas L.; Karanikolas, Breanne D. W.; Suetterlin, Christine; Overman, Larry E. [Journal of the American Chemical Society, 2011, vol. 133, # 43, p. 17494 - 17503]
[27]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2012/63126, 2012, A2 Location in patent: Page/Page column 25
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  • 7
  • [ 54664-61-8 ]
  • [ 60176-77-4 ]
  • [ 60410-16-4 ]
YieldReaction ConditionsOperation in experiment
95% With methanol; lipase B from Candida antarctica In tert-butyl methyl ether at 5℃; for 16h; Enzymatic reaction; enantioselective reaction; 4.6. Enzymatic transesterification of cis-3,5-Diacetoxy-1-cyclopentene cis-3,5-Diacetoxy-1-cyclopentene (10 g, 54.3 mmol) dissolved in MTBE (100 mL, 10 % w/v) and MeOH (4.4 mL, 100 mmol) were stirred at 150 rpm with immobilized enzyme (2 g, w/w) at 5 °C in a double walled glass reactor using an overhead mechanical stirrer. The reaction was followed by analysis on TLC and chiral GC. The reaction was complete in 16 h.
With sodium hydroxide In water at 32℃; for 8h; further enzymes; pH=7, phosphate buffer;
With N-(2-acetamido)-2-aminoethanesulfonic acid; ethanolamine; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 8h; antibody of IgG class: 37E8, pH 8.0; Km, Kcat, Ki; var. enzymes and time;
With sodium hydroxide In water at 32℃; for 8h; pH=7, phosphate buffer; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With sodium hydroxide In water for 8h; pH=7, phosphate buffer; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With N-(2-acetamido)-2-aminoethanesulfonic acid; ethanolamine; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 14h; antibody of IgG class: 37E8, pH 8.0; Title compound not separated from byproducts;
With pig liver esterase In phosphate buffer; ethanol at 37℃;

  • 8
  • [ 54664-61-8 ]
  • [ 115420-61-6 ]
YieldReaction ConditionsOperation in experiment
89.5% With osmium(VIII) oxide; trimethylamine-N-oxide In tetrahydrofuran; water; acetone for 15h; Ambient temperature;
With osmium(VIII) oxide; N-morpholine-N-oxide In acetone for 24h; Ambient temperature;
  • 9
  • [ 29783-26-4 ]
  • [ 108-24-7 ]
  • [ 54664-61-8 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In dichloromethane Ambient temperature;
97% With triethylamine In dichloromethane for 3h;
96.4% With dmap In pyridine; dichloromethane 1.) 0 deg C,; 2.) room temperature 13 h;
95% With pyridine; dmap at 20℃; for 1h;
86% With pyridine In dichloromethane Ambient temperature;
79% With pyridine; dmap for 0.5h; Ambient temperature;
20% With dmap In dichloromethane at 25℃;
Yield given;
With dmap; triethylamine In N,N-dimethyl-formamide at 10 - 30℃; for 16h; Inert atmosphere; 10 Cerium chloride heptahydrate (380 g) was dissolved in methanol (1700 ml) at 25-30°C and the resulting solution was cooled to -65°C, followed by the addition of 4-hydroxy-2- cyclopentenone (100 gm) at -70°C to -60°C. Sodium boro hydride (29 g) was added portion wise (in 5 portions) to the reaction mixture at -70°C to -60°C over a period of 60 minutes. The reaction mixture was stirred for 1 hour at -70°C to -60°C, followed by the addition of acetone (100 ml) at the same temperature over a period of 15 minutes to destroy the excess sodium borohydride. The temperature of the reaction mixture was raised to 25-30°C, followed by distillation of the mixture of methanol and acetone under vacuum at below 40°C and then stripping out methanol by using toluene (100 ml) at 40°C. N,N-dimethylformamide (1300 ml) was added to the resulting mass at 40°C and the resulting suspension was cooled to 25-30°C, followed by the addition of 4-dimethylamino pyridine (10 g) and triethylamine (825 g) under a nitrogen atmosphere. The suspension was cooled to 10°C under a nitrogen atmosphere, followed by drop wise addition of acetic anhydride (83 g) while maintaining the temperature at below 20°C over a period of 60 minutes. The reaction mixture was stirred for 15 hours at 25-30°C. Water (2 L) was added to the resulting mass at 25-30°C, followed by adjusting the pH to 2 by using dilute hydrochloric acid. The resulting mass was stirred for 15 minutes and then methylene dichloride (1000 ml) was added. The resulting mixture was stirred for 15 minutes, followed by separation of the water layer and then extracting with methylene dichloride (2 x 1 L). The combined organic layer was washed with water (2 x 1 L), and subsequently with 5% sodium bicarbonate (1 L) and water (2 x 1 L) at 25-30°C. The organic layer was dried over anhydrous sodium sulfate, followed by filtration and evaporation to dryness under reduced pressure to produce 160 g of crude product as a brown oil. The crude product was purified by fractional distillation column at 90°C under 5 mbar vacuum to produce 140 g of cis-3,5-diacetoxy-l-cyclopentene (Purity by GC: 96%).

  • 10
  • [ 108-24-7 ]
  • 6-oxabicyclo<3.1.0>hex-2-ene [ No CAS ]
  • [ 54664-61-8 ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0)
11 g With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 5h; Schlenk technique; Inert atmosphere;
  • 11
  • [ 542-92-7 ]
  • [ 64-19-7 ]
  • [ 54664-61-8 ]
YieldReaction ConditionsOperation in experiment
40% With manganese(IV) oxide; palladium diacetate; lithium acetate; p-benzoquinone; lithium chloride In water; pentane at 20℃; for 72h;
21% With lithium acetate; p-benzoquinone at 25℃; for 4h;
  • 12
  • [ 60410-17-5 ]
  • [ 64-19-7 ]
  • [ 54664-61-8 ]
YieldReaction ConditionsOperation in experiment
With 3 A molecular sieve; triphenylphosphine; diethylazodicarboxylate 1.) THF, room temp., 1 h, 2.) room temp., overnight; Yield given. Multistep reaction;
  • 13
  • [ 54664-61-8 ]
  • [ 2166-14-5 ]
  • dimethyl 5,7-bis(acetyloxy)-4a,5,6,7-tetrahydro-2H-cyclopenta[d]pyridazine-1,4-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98%
98% In dichloromethane at 20℃; for 96h;
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