Synthesis of, and NMR and CD studies on, methyl 4-O-[(R)- and (S)-1-carboxyethyl]-α-l-rhamnopyranoside and methyl 6-O-[(R)- and (S)-1-carboxyethyl]-α-d-galactopyranoside
✍ Scribed by Mats Andersson; Lennart Kenne; Roland Stenutz; Göran Widmalm
- Book ID
- 102998460
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 487 KB
- Volume
- 254
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
The title compounds were prepared by condensation of a suitably protected monosaccharide and (RI-or W2chloropropanoic acid. Characterization by 'H and 13C NMR spectroscopy revealed minor chemical shift differences between the diastereomers. CD spectra showed differences between the (RIand (S)-l-carboxyethyl substituted monosaccharides, thereby facilitating determination of the absolute configuration of the substituent.
📜 SIMILAR VOLUMES
As part of a programme involving X-ray crystallographic studies" of cis-and tpuns-fused hexopyranosides, we now report on the crystal structures of methyl 2-~-methyl-~-D-glucop~anoside\* (11, which was obtained by debe~lidenation of methyl 4,~-O-benzyIidene-2-O-methyI-3-O-~-tolylsulfonyl-~-~-glucopy