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Details van artikel 92 van 178 gevonden artikelen
| Titel: |
New N-Acylating Reagents Derived from 3-Deoxy-l-glycero-tetronic Acid1 |
| Auteur: |
Lei, Ping-sheng Ogawa, Yuji Kovac, Pavol |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 15 (1996) nr. 4 pagina's 485-500 |
| Jaar: |
1996-05-01 |
| Inhoud: |
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. |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 92 van 178 gevonden artikelen
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