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Chemical Structure| 388109-26-0 Chemical Structure| 388109-26-0

Structure of 388109-26-0

Chemical Structure| 388109-26-0

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Product Details of [ 388109-26-0 ]

CAS No. :388109-26-0
Formula : C8H12O4
M.W : 172.18
SMILES Code : O=C(C1C(COCC1)=O)OCC
MDL No. :MFCD19440853
InChI Key :APAWJCZGOJKZPB-UHFFFAOYSA-N
Pubchem ID :21362493

Safety of [ 388109-26-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 388109-26-0 ]

* 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.

  • Downstream synthetic route of [ 388109-26-0 ]

[ 388109-26-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 388109-26-0 ]
  • [ 3886-69-9 ]
  • ethyl 5-(((1R)-1-phenylethyl)amino)-3,6-dihydro-2H-pyran-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With p-toluenesulfonic acid monohydrate; In benzene; Part D. Preparation of (R)-5-(1-Phenyl-ethylamino)-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl ester A solution of <strong>[388109-26-0]3-oxo-tetrahydro-pyran-4-carboxylic acid ethyl ester</strong> (3.03 g, 17.6 mmol), R-(+)-alpha-methylbenzylamine (2.35 g, 19.4 mmol) and p-toluenesulfonic acid hydrate (67 mg, 230 mumol) in benzene (60 mL) was heated at reflux under a Dean-Stark trap for 16 h. The cooled mixture was concentrated in vacuo to provide the product as a yellow oily semisolid (5.05 g), used without further purification. 1H NMR (300 mHz, CDCl3) delta 8.97 (bd, J=7.3 Hz, 1H), 7.3-7.2 (m, 5H), 4.41 (m, 1H), 4.30 (d, J=16.1 Hz, 1H), 4.18 (q, J=7.3 Hz, 2H), 3.91 (d, J=16.1 Hz, 1H), 3.64 (m, 2H), 2.34 (m, 2H), 1.48 (d, J 6.5 Hz, 3H), 1.30 (t, J 7.3 Hz, 3H).
  • 2
  • [ 388109-26-0 ]
  • [ 388109-32-8 ]
  • 3
  • [ 388109-26-0 ]
  • [ 388109-34-0 ]
  • 4
  • [ 388109-26-0 ]
  • [ 388109-35-1 ]
  • 5
  • [ 388109-26-0 ]
  • [ 388109-37-3 ]
  • 6
  • [ 388109-26-0 ]
  • C25H33FN4O3S [ No CAS ]
  • 7
  • [ 388109-26-0 ]
  • ethyl (3S,4S)-3-(((1R)-1-phenylethyl)amino)tetrahydro-2H-pyran-4-carboxylate [ No CAS ]
  • 8
  • [ 388109-26-0 ]
  • [ 388109-30-6 ]
  • 9
  • [ 388109-23-7 ]
  • [ 388109-26-0 ]
YieldReaction ConditionsOperation in experiment
48% With potassium tert-butylate; In tetrahydrofuran; toluene; Part C. Preparation of 3-oxo-tetrahydro-pyran-4-carboxylic acid ethyl ester A solution of 4-ethoxycarbonylmethoxybutyric acid ethyl ester (90%, 15.0 g, 61.9 mmol) in toluene (300 mL) was stirred at room temperature and treated over 5 min with a solution of potassium tert-butoxide in tetrahydrofuran (1.0 M, 74.2 mL, 74.2 mmol). The mixture was stirred at room temperature for 24 h, then was poured into 1 N hydrochloric acid. The phases were separated, and the aqueous phase was extracted with ether. The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (5% ethyl acetate/hexanes) to provide the product as a pale yellow liquid (5.06 g, 48%). 1H NMR (300 mHz, CDCl3) delta 11.85 (s, 1H), 4.24 (q, J=7.3 Hz, 2H), 4.14 (t, J=1.7 Hz, 2H), 3.79 (t, J=5.5 Hz, 2H), 2.35 (tt, J=5.5, 1.7 Hz, 2H), 1.32 (t, J=7.3 Hz, 3H).
  • 10
  • [ 388109-26-0 ]
  • [ 38980-96-0 ]
  • [ 1450790-49-4 ]
  • 11
  • [ 388109-26-0 ]
  • 2-hydroxy-6-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)benzaldehyde [ No CAS ]
  • 12
  • [ 388109-26-0 ]
  • [ 1068522-32-6 ]
YieldReaction ConditionsOperation in experiment
With trifluoromethylsulfonic anhydride; Step 1: To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g).
With trifluoromethylsulfonic anhydride; Step 1 To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temeperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g).
  • 13
  • [ 388109-26-0 ]
  • ethyl 5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-carboxylate [ No CAS ]
  • 16
  • [ 388109-26-0 ]
  • 2-methoxy-5-[[5-(2-propan-2-ylpyrazol-3-yl)-3,6-dihydro-2H-pyran-4-yl]methoxy]pyridine-4-carbaldehyde [ No CAS ]
  • 17
  • [ 388109-26-0 ]
  • 2-hydroxy-6-[(5-phenyl-3,6-dihydro-2H-pyran-4-yl)methoxy]benzaldehyde [ No CAS ]
  • 18
  • [ 388109-26-0 ]
  • [ 1219633-05-2 ]
  • 19
  • [ 388109-26-0 ]
  • (5-phenyl-3,6-dihydro-2H-pyran-4-yl)methanol [ No CAS ]
  • 20
  • [ 388109-26-0 ]
  • 4-(bromomethyl)-5-phenyl-3,6-dihydro-2H-pyran [ No CAS ]
  • 21
  • [ 388109-26-0 ]
  • ethyl (3S,4R)-3-(1-isopropyl-1H-pyrazol-5-yl)tetrahydro-2H-pyran-4-carboxylate [ No CAS ]
  • 22
  • [ 388109-26-0 ]
  • (±) 2-hydroxy-6-(((3S,4R)-3-(1-isopropyl-1H-pyrazol-5-yl)tetrahydro-2H-pyran-4-yl)methoxy)benzaldehyde [ No CAS ]
  • 23
  • [ 388109-26-0 ]
  • (±)-ethyl (3S,4R)-3-(1-isopropyl-1H-pyrazol-5-yl)tetrahydro-2H-pyran-4-carboxylate [ No CAS ]
  • 24
  • [ 388109-26-0 ]
  • (±)-((3S,4R)-3-(1-isopropyl-1H-pyrazol-5-yl)tetrahydro-2H-pyran-4-yl)methanol [ No CAS ]
  • 25
  • [ 388109-26-0 ]
  • [ 358-23-6 ]
  • [ 1068522-32-6 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 4.5h;Inert atmosphere; To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.01 g, 5.58 mmol,) dissolved in DCM (28 mL) and cooled under N2 to -78C, was added DIPEA (1.2 mL, 6.9 mmol). The reaction mixture was stirred under N2, then a 1M solution of trifluoromethanesulfonic anhydride in DCM (6.07 mL, 6.07 mmol) was added. The reaction mixture was stirred at -78C for 30 minutes, then warmed to r.t. and stirred for 4 h. Saturated aqueous NaHCO3 solution (30 mL) was added. The mixture was stirred rapidly at room temperature for 5 minutes, then filtered. The organic layer was concentrated in vacuo to afford ethyl 5-(trifluoromethylsulfonyloxy)-3,6-dihydro-2H- pyran-4-carboxylate (1.7 g, quantitative) as a brown oil.
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 2.0h; Step 1 To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2g).
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 2.0h; O1 161 Step 1: i?o a solution of eth I 3-oxotetrahvdro2i 1.p ran-4-?carhoxvlate (1 0 g, 5.8mmo )in 1X?M (30 mu was added D1PI.A 1 .22 ml., 6.97 mmcl) and FfO (1 08 ml., 6.39mmoi at 78 C. then it us warmed up to room temperature and stirred at roomtemepemature fhr 2 h, the o1ution as diluted with DCM, ashcd with Sat. aH(O, brine.dried and concentated to give eih3 I 5?1((trifluoronieth l)sulton I oxy).?3,6?dih dio-21 lp mam4-cai boxy late as crude product (2 ,
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 2.0h; Step 1:To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g).
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (4.40 g, 25.50 mmol) and DIEA (13.21 ml, 76.66 mmol) in 120 ml of DCM at 0 C was added triflic anhydride (4.62 ml, 28.11 mmol) and the mixture was allowed to stir overnight at room temperature. DCM was removed under vacuum and the residue dissolved in EtOAc and washed with 1 N HCI and then brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluting with 20% EtOAc/heptane to yield ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H- pyran-4-carboxylate as a light brown oil. Mass spectrum (ESI, m/z): Calculated for C9H11F3O6S, 305.2 (M+H), Measured 305.0.

  • 26
  • [ 388109-26-0 ]
  • [ 407-25-0 ]
  • [ 1068522-32-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 2.0h; Step 1 To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g).
  • 27
  • [ 388109-26-0 ]
  • tert-butyl 2-(5-amino-1H-pyrazol-3-yl)piperidine-1-carboxylate [ No CAS ]
  • tert-butyl 2-(9-hydroxy-7,8-dihydro-5H-pyrano[3,4-d]pyrazolo[1,5-a]pyrimidin-2-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With acetic acid; In ethanol; for 2.0h;Reflux; To the intermediate 4 (500 mg, 1.87 mmol) in EtOH (50 mL), ethyl 3-oxotetrahydro-2H- pyran-4-carboxylate (0.55 mL, 3.74 mmol, 2 eq.) and AcOH (1.07 mL, 18.69 mmol, 10 eq.) were added. The reaction mixture was stirred at reflux for 2 hours then cooled to room temperature and evaporated under reduce pressure. The residue was triturated in DIPE. Theprecipitate was filtered to give intermediate 44 (675 mg, 100 % pure, 96 % yield).LCMS (M + 1) = 375.1H NMR (400 MHz, DMSO-d6) oe ppm 1.31 - 1.47 (m, 11 H) 1.56 (br. s., 2 H) 1.70 (d,J5.06 Hz, 1 H) 2.32 (d, J12.98 Hz, 1 H) 2.44 - 2.48 (m, 2 H) 2.70 - 2.88 (m, 1 H) 3.81 -3.96 (m, 3 H) 4.51 (s, 2 H) 5.32 (br. s., 1 H) 5.77 (s, 1 H) 12.08 (br. s., 1 H).
  • 28
  • [ 388109-26-0 ]
  • ethyl 5-amino-3,6-dihydro-2H-pyran-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium carbamate; In methanol; at 25℃; for 2.0h; A mixture of methyl 5-(3-methoxy-3-oxopropyl)tetrahydrofuran-2-carboxylate (3 g, 17.4 mmol) and H4OCO H2 (2.65 g, 34.9 mmol) in MeOH (20 mL) was stirred at 25C for 2 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with 5: 1 petroleum ether/ethyl acetate) to give the product. XH MR (400MHz, CD3OD) delta 4.17 - 4.03 (m, 4H), 3.73 (t, J=5.5 Hz, 2H), 2.37 - 2.19 (m, 2H), 1.24 (t, J=7.0 Hz, 3H).
  • 29
  • [ 388109-26-0 ]
  • ethyl 5-(3-methoxy-3-oxopropanamido)-3,6-dihydro-2H-pyran-4-carboxylate [ No CAS ]
  • 30
  • [ 388109-26-0 ]
  • methyl 2,4-dihydroxy-6,8-dihydro-5H-pyrano[3,4-b]pyridine-3-carboxylate [ No CAS ]
  • 31
  • [ 388109-26-0 ]
  • 6,8-dihydro-5H-pyrano[3,4-b]pyridine-2,4-diol [ No CAS ]
  • 32
  • [ 388109-26-0 ]
  • 2,4-dichloro-6,8-dihydro-5H-pyrano[3,4-b]pyridine [ No CAS ]
  • 33
  • [ 388109-26-0 ]
  • ethyl 4-chloro-6,8-dihydro-5H-pyrano[3,4-b]pyridine-2-carboxylate [ No CAS ]
  • 34
  • [ 388109-26-0 ]
  • ethyl 4-(2,4-difluorophenyl)-6,8-dihydro-5H-pyrano[3,4-b]pyridine-2-carboxylate [ No CAS ]
  • 35
  • [ 388109-26-0 ]
  • 4-(2,4-difluorophenyl)-6,8-dihydro-5H-pyrano[3,4-b]pyridine-2-carboxamide [ No CAS ]
 

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