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Chemical Structure| 7605-25-6 Chemical Structure| 7605-25-6

Structure of 7605-25-6

Chemical Structure| 7605-25-6

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Product Citations

Product Citations

Siriboe, Mary G ; Vargas, David A ; Fasan, Rudi ;

Abstract: Chiral cyclopropanols are highly desirable building blocks for medicinal chemistry, but the stereoselective synthesis of these molecules remains challenging. Here, a novel strategy is reported for the diastereo- and enantioselective synthesis of cyclopropanol derivatives via the biocatalytic asymmetric cyclopropanation of vinyl esters with ethyl diazoacetate (EDA). A dehaloperoxidase enzyme from Amphitrite ornata was repurposed to catalyze this challenging cyclopropanation reaction, and its activity and stereoselectivity were optimized via protein engineering. Using this system, a broad range of electron-deficient vinyl esters were efficiently converted to the desired cyclopropanation products with up to 99.5:0.5 diastereomeric and enantiomeric ratios. In addition, the engineered dehaloperoxidase-based biocatalyst is able to catalyze a variety of other abiological carbene transfer reactions, including N−H/S−H carbene insertion with EDA as well as cyclopropanation with diazoacetonitrile, thus adding to the multifunctionality of this enzyme and defining it as a valuable new scaffold for the development of novel carbene transferases.

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Product Details of [ 7605-25-6 ]

CAS No. :7605-25-6
Formula : C10H12O2S
M.W : 196.27
SMILES Code : O=C(OCC)CSC1=CC=CC=C1
MDL No. :MFCD00145107
InChI Key :SEDRTXNDGKRHBL-UHFFFAOYSA-N
Pubchem ID :97312

Safety of [ 7605-25-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of [ 7605-25-6 ]

* 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 [ 7605-25-6 ]

[ 7605-25-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 7605-25-6 ]
  • [ 143982-39-2 ]
  • ethyl (Z)-3-(8-methylimidazo<1,2-a>pyrid-2-yl)-2-phenylthioacrylate [ No CAS ]
  • 2
  • [ 696-63-9 ]
  • [ 105-36-2 ]
  • [ 7605-25-6 ]
  • [ 28743-98-8 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate; Ethyl (4-methoxyphenylthio)acetate may be prepared in the following manner: The procedure is as in Example 2 for the preparation of ethyl (phenylthio)acetate starting with ethyl bromoacetate (11.7 g), a 2M ethanolic solution of sodium ethylate (35 cc) and 4-methoxythiophenol (10 g). Ethyl (4-methoxyphenylthio)acetate (13.6 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.
 

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