22132-85-0Relevant academic research and scientific papers
Inositol to aromatics –benzene free synthesis of poly oxygenated aromatics
Gurale, Bharat P.,Shashidhar, Mysore S.,Sardessai, Richa S.,Gonnade, Rajesh G.
, p. 38 - 44 (2018/03/26)
A method for the preparation of benzene derivatives from myo-inositol, an abundantly available phyto chemical is described. 1,3-Bridged acetals of inososes undergo step-wise elimination leading to the formation of polyoxygenated benzene derivatives. This aromatization reaction proceeds through the intermediacy of a β-alkoxyenone, which could be isolated. This sequence of reactions starting from myo-inositol, provides a novel route for the preparation of polyoxygenated benzene derivatives including polyoxygenated biphenyl. This scheme of synthesis demonstrates the potential of myo-inositol as a sustainable non-petrochemical resource for aromatic compounds.
An expansion of the role of the coreylink reaction for the synthesis of α-substituted carboxylic acid esters
Scaffidi, Adrian,Skelton, Brian W.,Stick, Robert V.,White, Allan H.
, p. 426 - 433 (2007/10/03)
The treatment of 1,2:5,6-di-O-isopropylidene-?-d-ribo-hexos-3-ulose with chloroform under basic conditions has yielded the normal 3-C-trichloromethyl-?- d-allofuranose derivative. Under the conditions of the modified Corey?Link reaction but with a nucleophile different from the usual azide, a range of ?-substituted carboxylic acid esters (and one amide) has been obtained. A similar addition of bromoform to the ulose has formed the ?-bromo methyl ester. Two attempts at forming an ?inositol ?-amino acid' from a polyhydroxylated cyclohexanone failed. Single-crystal X-ray structure determinations are reported for (3S)-1,2:5,6-di-O-isopropylidene-3-C-methoxycarbonyl-3-S-phenyl-3-thio-?-d- ribo-hexose, (3S)-1,2:5,6-di-O-isopropylidene-3-S-phenyl-3-C-(phenylthio) carbonyl-3-thio-?-d-ribo-hexose, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-C- methoxycarbonyl-?-d-erythro-hex-3-enofuranose, 4,6-di-O-benzyl-2-C- trichloromethyl-scyllo-inositol 1,3,5-orthoformate, 2,2'-anhydro-4,6-di-O- benzyl-2-C-dichlorohydroxymethyl-scyllo-inositol 1,3,5-orthoformate, 1,3,4,5,6-penta-O-benzyl-2-C-trichloromethyl-myo-inositol, and 2-amino-1,3,4,5,6-penta-O-benzyl-2-C-cyano-2-deoxy-myo-inositol. CSIRO 2006.
THE SYNTHESIS OF (+/-)MYO-INOSITOL-1-PHOSPHONATE
Kulagowski, Janusz J.
, p. 3869 - 3872 (2007/10/02)
The synthesis of a phosphonate analogue of (+/-)-myo-inositol-1-phosphate using Horner-Emmons methodology is described.
