616876-80-3Relevant academic research and scientific papers
Concerning Tishchenko-like side products in oxidation of hydroxymethyl to formyl groups
Guo, Zhiwei,Padmakumar, Raghavakaimal,Hollingsworth, Rawle I.,Radhakrishnan,Nandakumar,Fraser-Reid, Bert
, p. 1067 - 1069 (2007/10/03)
Oxidation of a hydroxymethyl group to an aldehyde sometimes gives a dimeric ester reminiscent of a Tishchenko aldehyde-ester disproportionation. This process has been observed only with Cr(VI)/pyridine based reagents, and can be avoided most notably by us
New N-acylating reagents derived from 3-deoxy-L-glycero-tetronic acid
Lei, Ping-Sheng,Ogawa, Yuji,Kovac, Pavol
, p. 485 - 500 (2007/10/03)
Commercially available N-Boc-4-O-benzyl-L-homoserine was treated with trifluoroacetic acid and the corresponding, N-deprotected derivative was submitted to deamination to give 4-O-benzyl-3-deoxy-L-glycero-tetronic acid (5). In another approach to 3-deoxy-L-glycero-tetronic acid protected at position 4, the carboxylic groups in L-malic acid were reduced, and the resulting triol was benzylidenated. Oxidation of the 2,4-O-benzylidene derivative formed with CrO3-pyridine complex in the presence of t-butyl alcohol gave t-butyl 2,4-O-benzylidene-3-deoxy-L-glycero-tetronate (13). The latter was saponified with aqueous sodium hydroxide to give, after Na+ exchange for H+, 2,4-O-benzylidene-3-deoxy-L-glycero-tetronic acid (15). Opening of the acetal ring in 13, followed by hydrolytic cleavage of the t-butyl ester function gave material indistinguishable from 5 obtained in the original way. When tested for their efficiency of N-acylation of derivatives of D-perosamine, both acids 5 and 15 gave the corresponding tetronamido derivatives in high yields.
