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[ CAS No. 1204220-63-2 ] {[proInfo.proName]}

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Chemical Structure| 1204220-63-2
Chemical Structure| 1204220-63-2
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Product Details of [ 1204220-63-2 ]

CAS No. :1204220-63-2 MDL No. :
Formula : C20H23ClO7 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 410.85 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1204220-63-2 ]

* 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 [ 1204220-63-2 ]

[ 1204220-63-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 6579-54-0 ]
  • [ 1204220-63-2 ]
  • [ 1298086-14-2 ]
YieldReaction ConditionsOperation in experiment
66% With triethylamine; zinc dibromide; In 2-methyltetrahydrofuran; at 0 - 20℃; To a solution of [(2S,3R,4S,5S,6R)-2-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-6- hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol (4.2 g, 10.22 mmol) dissolved in 2-methyl tetrahydrofuran (40 mL) and cooled to 0 degrees Celsius was addedtriethylamine (4.27 mL, 30.7 mmol), zinc bromide (6.53 g, 26.6 mmol) followed byportionwise addition 2,6-dichlorobenzenesulfonyl chlroride (0.610 g, 2.48 mmol). The reaction mixture was warmed to room temperature and allowed to stir overnight (-16 hours). The reaction was quenched by addition of an aqueous solution of 1hydrochloric acid (100 mL) and water (100 mL). The reaction mixture was extracted using ethyl acetate (100 mL) and the aqueous layer was extracted with ethyl acetate(100 mL) an additional time. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. 5.6g(66% yield) of the desired product obtained as an off white solid. 1H NMR (400 MHz, METHANOL-^) delta ppm 3.00 (s, 3 H), 3.03 (d, .J=9.4 Hz, 1 H), 3.38 (t, J=9.5 Hz, 1 H), 3.71 (t, J=9.2 Hz, 1 H), 3.79 (ddd, .7=10.1, 5.9, 1.5 Hz, 1 H), 4.00 - 4.14 (m, 2 H), 4.43 (dd, J=10.7, 5.9 Hz, 1 H), 4.55 (dd, J=10.8, 1.5 Hz, 1 H), 7.01 (d, J=8.6 Hz, 2 H), 7.16 (d, J=8.6 Hz, 2 H), 7.24 - 7.30 (m, 1 H), 7.31 - 7.36 (m, 1 H), 7.44 - 7.61 (m, 7 H).
  • 2
  • [ 1204220-63-2 ]
  • [ 864070-37-1 ]
YieldReaction ConditionsOperation in experiment
60% With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at -30 - -10℃; for 2h; Inert atmosphere;
38% With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at -10 - 0℃; for 4h; 4 1-Chloro-4-(β-D-glycopyranose-1-yl)-2-(4-hydroxy-benzyl)benzene EXAMPLE 4 1-Chloro-4-(β-D-glycopyranose-1-yl)-2-(4-hydroxy-benzyl)benzene A solution of the 1-chloro-4-(1-methoxy-D-glucopyranose-1-yl)-2-(4-hydroxybenzyl)benzene (1.06 g, 2.83 mmol) in CH2Cl2/CH3CN (1:1, 24 mL) gained above was cooled to -10° C. After addition of triethylsilane (660 mg, 5.66 mmol), BF3.Et2O (1.1 mL, 3.98 mmol) was added dropwise to the mixture at a rate that the reaction temperature was maintained below -5° C. When the addition finished, the mixture was stirred for 4 hours at 0° C. The reaction was then quenched by the addition of saturated aqueous sodium bicarbonate (50 mL). The organic phase was seperated and the aqueous phase was extracted for 3 times with ethyl acetate. The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum. The residue was purified by silica gel column chromatography (dichloromethane/methanol, 15:1) to afford the target compound. Yield: 0.37 g (38% of theoretical value). 1HNMR (500 MHz, CD3OD) δ: 7.16-7.25 (m, 3H), 6.91 (d, J=8.5 HZ, 2H), 6.58 (d, J=8.5 HZ, 2H), 3.97-4.01 (m, 1H), 3.89 (dd, J=15 Hz, 13 Hz, 2H), 3.77 (d, J=11 Hz, 1H), 3.57-3.60 (m, 1H), 3.28-3.35 (m, 3H), 3.17-3.21 (m, 1H). LC-MS (ESI): m/z=403/405 (Cl) [M+Na]+.
2.67 g With triethylsilane; aluminum (III) chloride In dichloromethane; acetonitrile at 5℃; for 1h; Cooling with ice; 4; 7; 8 The methyl glycoside intermediate was dissolved in a mixed solvent of 10 mL of acetonitrile and 10 mL of dichloromethane, and anhydrous aluminum trichloride (2.67 g, 20.0 mmol, 2.0 eq.) was added. Slowly add triethylsilane (Et3SiH) under ice water bath conditions (3.56g, 30.0mmol, 3.0eq.), The reaction system temperature is below 5 ° C, after the dropwise addition was completed, the reaction was stirred for 1 hour while the ice-water mixture was cooled. TLC monitoring showed that the indole intermediate was basically converted. Carefully quench the reaction with 10 mL of deionized water, dispense, The aqueous phase was extracted with dichloromethane (20 mL×3) and the organic phases were combined.Wash with saturated brine (20 mL), dry over anhydrous sodium The filtrate was evaporated under reduced pressure to remove the solvent. Obtaining a yellow oily product, Separation and purification by column chromatography gave a white solid white solid. That is, empagliflozin dehydrotetramethane impurity 2.67 g (7.0 mmol, yield 70.0%).
  • 3
  • [ 915095-86-2 ]
  • [ 1204220-63-2 ]
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