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[ CAS No. 147126-62-3 ] {[proInfo.proName]}

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Chemical Structure| 147126-62-3
Chemical Structure| 147126-62-3
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Product Details of [ 147126-62-3 ]

CAS No. :147126-62-3 MDL No. :MFCD08273790
Formula : C14H24O4S Boiling Point : -
Linear Structure Formula :- InChI Key :KXKDZLRTIFHOHW-CYRBOEJBSA-N
M.W : 288.40 Pubchem ID :15383325
Synonyms :

Safety of [ 147126-62-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 147126-62-3 ]

* 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 [ 147126-62-3 ]
  • Downstream synthetic route of [ 147126-62-3 ]

[ 147126-62-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 40018-26-6 ]
  • [ 111969-64-3 ]
  • [ 147126-62-3 ]
YieldReaction ConditionsOperation in experiment
88% With acetic acid In acetone at 50 - 125℃; L-Menthyl glyoxalate monohydrate (1.0 g, 4.34 mmol) in acetone (10 mL), was added to 1,4-dithiane 2,5-diol (396 mg, 2.60 mmol) and a catalytic amount of acetic acid (0.5 mL). The solutions were pumped at a flow rate 0.05 mL/min (for a combined flow rate of 0.1 mL/min, and the reaction solution was passed through a flow reactor at 125°C, and exited the flow system through a back pressure regulator (lObar) to control the temperature and pressure. The reaction mixture was collected into a collection vial equipped with a septum. After completion of the reaction, as monitored by thin layer chromatography (“TLC”) and gas chromatography (“GC”), the solvent was evaporated. The reaction mixture was cooled to 0°C - 5°C and a 1percent triethylamine in heptane or hexane solution was added drop wise. The mixture was stirred at 0°C for 2 — 3 hours, observing the formation of precipitation. The isolated solid was filtered and washed with n-hexane to give (2R,5R)-((1 R, 2S,5R)-2-isopropyl-5- methylcyclohexyl) 5-hydroxy-1, 3-oxathiolane-2-carboxylate (1.1 g, 88percent) as a white solid. Spectral Analysis:IH-NMR in CDCI3 (400 MHz): a 5.96 (ci, IH), 5.57 (d, IH), 4.74 (s, IH), 3.32-3.29 (m, IH), 3.17-3.08 (dd, IH), 2.02 (d, 2H), 1.70 (d, 1H), 1.51 -1 .42 (m, 2H),1.09-1.00 (m, 21-I), 0.91(d, 61-1), 0.78 (d, 3H). 13C-NMR in CDCI3 (100 MHz): B16.27, 20.69, 23.30, 26.16, 31.42, 34.11, 38.46, 40.35, 46.86, 46.07, 80.20,101.22, 103.20, 172.18. FT-IR (Neat): 3456, 2956, 2864, 1731, 1457, 1387,1288, 1196, 1041, 986.Nature of the compound: white solidFlow rate: 0.1 mLlminResidence Time: 20 mmReaction temperature: 50 °C to 125 °CRecrystallization: 1percent in TEA in heptane/hexaneConfirmed by: GC, IR and 1H-NMR spectra
100 g With acetic acid In toluene at 50 - 115℃; L-menthyl glyoxylate hydrate (prepared by reaction of L-menthol with glyoxalic acid as per process described in Synthetic Commun., 1990, 20, 2837-2847 by Fernadez F.) (100 gm, 0.434 mol, 1 molar equivalents), toluene (500 ml) and acetic acid (10 ml) were mixed under stirring and thus formed reaction mixture was heated up to 1 10- 1 15°C, to remove water azeotropically. The reaction mixture was cooled up to 80°C and solvent was distilled under vacuum up to the final volume becomes 300 ml. The reaction mixture was cooled to 50°C and 1 ,4-Dithiane 2,5-Diol (33.1 gm, 0.217 mol, 2 molar equivalents) was added. The reaction mixture was refluxed (110- 115°C) and monitored the reaction by TLC. The mixture was cooled to 0-5°C after completion of the reaction. 600 ml of 10percent triethylamine in n-heptane was added to the reaction mixture drop wise over a period of an hour. The mixture was then maintained at 0-5°C for an hour to form a solid. The isolated solid was filtered, washed with n-heptane and dried. Yield: 100 g. Ή NMR (DMSO-d6 + D20) δ (ppm): 0.70-0.91 (m, 10H); 0.95- 1.05 (q, 2H), 1.35- 1.46 (q, 2H), 1.62- 1.64 (d, 2H), 1.84- 1.90 (t, 2H), 2.86-2.88 (d, 1H), 3.12-3.16 (q, 1H), 4.59-4.64 (m, 1H), 5.55-5.60 (t, 1H), 5.86 (s, 1H), 7.03-7.04 (d, 1H); i3C NMR (DMSO-d6) 8 (ppm): 21 , 22.2, 23.3, 26, 31.2, 34, 37.8, 38, 40.1 , 46.7, 75, 76.4, 102.4, 169.5; IR (KBr) (cm-'): 3470, 2962, 29.34, 28.366, 1734, 1465, 1 198, 1077, 1041, 902, 516; MS (EI) m/z = 287.3 (M- l).
Reference: [1] Patent: WO2017/216709, 2017, A2, . Location in patent: Page/Page column 12; 13; 14; 15; 17; 18
[2] Tetrahedron Letters, 2005, vol. 46, # 49, p. 8535 - 8538
[3] Patent: WO2013/21290, 2013, A1, . Location in patent: Page/Page column 17; 18
  • 2
  • [ 147126-62-3 ]
  • [ 764659-72-5 ]
Reference: [1] Patent: WO2011/83484, 2011, A2,
  • 3
  • [ 108-24-7 ]
  • [ 147126-62-3 ]
  • [ 147126-65-6 ]
  • [ 147027-09-6 ]
YieldReaction ConditionsOperation in experiment
>= 80 % de With pyridine In di-isopropyl ether at 0 - 8℃; for 10 h; Inert atmosphere EXAMPLE 5
Preparation of (1'R,2'S,5'R)-menthyl-5(RS)-acetoxy-1,3-oxathio-lane-2R-carboxylate
To a precooled suspension of (1'R,2'S,5R)-menthyl-5R-hydroxy-1,3-oxathiolane-2R-carboxylate (Hydroxy compound, 300 g, 1.04 mol) in diisopropyl ether (1050 ml) at 0-5° C., pyridine (103.5 g, 1.31 mol) and 4-dimethylaminopyridine (0.35 g, 3 mmoles) was added under nitrogen.
Acetic anhydride (123.6 g, 1.21 mol) was diluted with diisopropyl ether (380 ml) and added to reaction mass at 0-8° C. in ~2 h.
Stirring of reaction mass was continued at 3-8° C. for 10 h to complete the reaction.
After completion of reaction (checked by TLC), the reaction mass was heated to RT (20-30° C.) and diluted with diisopropyl ether (350 ml).
Thereafter, reaction mass was washed with 5percent v/v aqueous acetic acid (2*400 ml) followed by with warm water (2*500 ml, ~40° C.) to ensure complete removal of pyridine.
Organic layer was concentrated under reduced pressure at less than 45° C. to obtain a solid residue.
To the residue hexanes (390 ml) was added and the contents were heated to ~50° C. and maintained for 15-20 min at same temperature.
Thereafter, it was cooled to RT and stirred for ~30 min.
Further, the product slurry was cooled to -6° C. to -10° C. and stirred for 3 h at the same temperature.
Product was filtered and washed with prechilled hexanes (150 ml, -6° C. to -8° C.).
Product was dried at ~45° C. under reduced pressure for 6 h to give title compound.
Yield: 279.6 g
Chromatographic purity (By HPLC, RI-Detector): 99.87percent
The product obtained was mixture of (2R,5R) and (2R,5S) isomers with (2R,5R) being the predominant (≧90percent) and (2R,5S) being the minor component (≦10percent) [by HPLC analysis, RI-detector].
It has been observed during coupled ester preparation that isomer ratio of acetoxy compound has no effect on the ratio of α:β isomers formation in glycosidation reaction.
Reference: [1] Patent: WO2010/82128, 2010, A1, . Location in patent: Page/Page column 22
[2] Patent: US2011/282046, 2011, A1, . Location in patent: Page/Page column 9
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