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]
^David Crich (2010). "Mechanism of a Chemical Glycosylation Reaction". Acc. Chem. Res. 43 (8): 1144–1153. doi:10.1021/ar100035r. PMID 20496888.
^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.
^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.
^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.
and 10 Related for: Benzylidene acetal information
chemistry, a benzylideneacetal is the functional group with the structural formula C6H5CH(OR)2 (R = alkyl, aryl). Benzylideneacetals are used as protecting...
example of a polyacetal. Benzylideneacetal and acetonide as protecting groups used in research of modified sugars. Acetals also find application as chiral...
Benzylidene compounds are, formally speaking, derivatives of benzylidene, although few are prepared from the carbene. Benzylideneacetal is a protecting...
codependently as an acetal. Common in this situation are the benzylidene, isopropylidene and cyclohexylidene or cyclopentylidene acetals. An exceptional case...
With diols, including many sugars, benzaldehyde condenses to form benzylideneacetals. Benzaldehyde is commonly employed to confer almond flavor to foods...
2-hydroxylamine group of Ser or Thr leads to the formation of an N,O-benzylideneacetal-linked intermediate, which undergoes acidolysis to afford a natural...
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...
Akiyama, M.; Sato, S.; Ogasawara, K. (1983). "A Facile Cleavage of BenzylideneAcetals with Diisobutylaluminum Hydride" (pdf). Chemistry Letters. 12 (10):...
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