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Chemical Structure| 81058-27-7 Chemical Structure| 81058-27-7
Chemical Structure| 81058-27-7

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Product Details of 2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide

CAS No. :81058-27-7
Formula : C26H43BrO9
M.W : 579.52
SMILES Code : CC(C)(C)C(OC[C@@H]1[C@@H](OC(C(C)(C)C)=O)[C@H](OC(C(C)(C)C)=O)[C@@H](OC(C(C)(C)C)=O)[C@@H](Br)O1)=O
MDL No. :MFCD08275217

Safety of 2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of 2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide

* 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 [ 81058-27-7 ]

[ 81058-27-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1743-60-8 ]
  • [ 81058-27-7 ]
  • [ 100083-88-3 ]
  • 2
  • [ 915095-89-5 ]
  • [ 81058-27-7 ]
  • C43H59ClO11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% A three-necked flask was charged with a compound of formula 5a (36.77 g, 100 mmol)And tetrahydrofuran (184 mL),Stirring and dissolving the ice salt bath after cooling to -10 ~ 0 ,Vacuum switching nitrogen 3 times,1.0M isopropylmagnesium chloride chloride lithium chloride complex tetrahydrofuran was added dropwiseSolution (105 mmol, 105 mL),Stirring 10 to 15 minutes after the drop of n-butyl lithium tetrahydrofuran solution, incubation reaction 1 to 2 hours standby.The reaction flask was charged with compound 6b (63.75 g, 110 mmol) and iron acetylacetonate (1.77 g, 5.0 mmol)Under nitrogen, tetrahydrofuran (184 mL) was added,The above prepared Grignard reagent solution was dropped into the reaction flask,And then heated to 40 ~ 50 reaction 6 to 8 hours,The reaction was quenched by the addition of dilute hydrochloric acid (2 mol / L, 184 mL) and the mixture was extracted three times with ethyl acetate (220 mL)The combined organic phases were washed twice with water (184 mL)Sodium sulfate,filter,After concentrating, the residue was recrystallized from a mixed solvent of ethyl acetate petroleum ether to give 7b (52.75 g, 67%).The lithium chloride complex of isopropylmagnesium chloride can be replaced by isopropylmagnesium chloride, cyclohexylmagnesium chloride or n-butylmagnesium chloride or their complex with lithium chloride, or butyllithium, The neutral butyl lithium reaction is directly removed from the halogen to give the aryl lithium reagent instead. The reaction solvent tetrahydrofuran can be replaced by 2-methyltetrahydrofuran, toluene or methylene chloride. The catalyst acetylacetonate can be treated with ferric chloride, nickel acetylacetonate, nickel dichloride, nickel dichloride ethylene glycol complex or bis Phenylphosphine) nickel dichloride instead.
 

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