New N-acylating reagents derived from 3-deoxy-L-glycero-tetronic acid

Article abstract of DOI:10.1080/07328309608005668

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.

Full text of DOI:10.1080/07328309608005668

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New N-Acylating Reagents Derived from
3-Deoxy-l-glycero-tetronic Acid1
a
Ping-sheng Lei a , Yuji Ogawa a & Pavol Kováč
a NIDDK, National Institutes of Health , 8 Center Drive, Bethesda,
Maryland, 20892-0815, U.S.A.
Published online: 22 Aug 2006.
To cite this article: Ping-sheng Lei , Yuji Ogawa & Pavol Kováč (1996) New N-Acylating Reagents
Derived from 3-Deoxy-l-glycero-tetronic Acid1 , Journal of Carbohydrate Chemistry, 15:4, 485-500,
DOI: 10.1080/07328309608005668
To link to this article: http://dx.doi.org/10.1080/07328309608005668
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