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Benzylidene acetal information


Structure of the benzylidene acetal of glucose.

In organic chemistry, a benzylidene acetal is the functional group with the structural formula C6H5CH(OR)2 (R = alkyl, aryl). Benzylidene acetals are used as protecting groups in glycochemistry.[1][2] These compounds can also be oxidized to carboxylic acids in order to open important biological molecules, such as glycosaminoglycans, to other routes of synthesis.[3] They arise from the reaction of a 1,2- or 1,3-diols with benzaldehyde. Other aromatic aldehydes are also used.[4]

  1. ^ David Crich (2010). "Mechanism of a Chemical Glycosylation Reaction". Acc. Chem. Res. 43 (8): 1144–1153. doi:10.1021/ar100035r. PMID 20496888.
  2. ^ S. Hanessian (1987). "6-Bromo-6-deoxy Hexose Derivatives By Ring Opening Of Benzylidene Acetals With N-bromosuccinimide: Methyl 4-o-benzoyl-6-bromo-6-deoxy-α-d-glucopyranoside". Org. Synth. 65: 243. doi:10.15227/orgsyn.065.0243.
  3. ^ Banerjee, Amit; Senthilkumar, Soundararasu; Baskaran, Sundarababu (2015-12-07). "Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids". Chemistry - A European Journal. 22 (3): 902–906. doi:10.1002/chem.201503998. ISSN 0947-6539. PMID 26572799.
  4. ^ Hiroyuki Osajima; Hideto Fujiwara; Kentaro Okano; Hidetoshi Tokuyama; Tohru Fukuyama (2009). "Protection Of Diols With 4-(Tert-butyldimethylsilyloxy)benzylidene Acetal And Its Deprotection". Org. Synth. 86: 130. doi:10.15227/orgsyn.086.0130.

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Benzylidene acetal

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chemistry, a benzylidene acetal is the functional group with the structural formula C6H5CH(OR)2 (R = alkyl, aryl). Benzylidene acetals are used as protecting...

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Acetal

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example of a polyacetal. Benzylidene acetal and acetonide as protecting groups used in research of modified sugars. Acetals also find application as chiral...

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Benzylidene compounds

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Benzylidene compounds are, formally speaking, derivatives of benzylidene, although few are prepared from the carbene. Benzylidene acetal is a protecting...

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Protecting group

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codependently as an acetal. Common in this situation are the benzylidene, isopropylidene and cyclohexylidene or cyclopentylidene acetals. An exceptional case...

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Benzaldehyde

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With diols, including many sugars, benzaldehyde condenses to form benzylidene acetals. Benzaldehyde is commonly employed to confer almond flavor to foods...

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Chemical ligation

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2-hydroxylamine group of Ser or Thr leads to the formation of an N,O-benzylidene acetal-linked intermediate, which undergoes acidolysis to afford a natural...

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Diol

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used so that the functional group does not react to future reactions. Benzylidene groups are used to protect 1,3-diols. There are extremely useful in biochemistry...

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Aluminium hydride

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Akiyama, M.; Sato, S.; Ogasawara, K. (1983). "A Facile Cleavage of Benzylidene Acetals with Diisobutylaluminum Hydride" (pdf). Chemistry Letters. 12 (10):...

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Mark Cushman

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Castagnoli, Neal (1969-10-01). "Condensation of succinic anhydride with N-benzylidene-N-methylamine. Stereoselective synthesis of trans- and...

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List of compounds with carbon number 9

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phosphaferrocene 63287-55-8 C9H9N benzenepropanenitrile 645-59-0 C9H9NO benzylidene acetamide 621-79-4 C9H9NO cinnamaldehyde oxime 13372-81-1 C9H9NO3 malonanilic...

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