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d-Galactose-derived d-galacturonic acid derivatives suitable as glycosyl acceptors

✍ Scribed by Wolfram Steffan; Christian Vogel; Helmut Kristen

Book ID
102993652
Publisher
Elsevier Science
Year
1990
Tongue
English
Weight
976 KB
Volume
204
Category
Article
ISSN
0008-6215

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✦ Synopsis

Ally1 (la) and benzyl (lb) B-D-galactopyranosides were converted into methyl [ally1 (and benzyl) 2-0-acetyl-3,4-O-isopropylidene-B-o-galactopyranosid]uronates, (6a and 6b) by three different routes. The carboxyl group was introduced by Jones oxidation of suitably protected precursors and esterified directly. The chemical behaviour of 6-0-trityl-, 6-O-(4,4'-dimethoxytrityl)-, and 6-O-(2-methoxypropane-2-yl)derivatives was investigated. The overall yields obtained were strongly influenced by the protecting groups used, in particular their stability in acidic solution.

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An efficient and highly stereoselective
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Galacturonic Acid Derivatives, VIII. Synthesis ofN-(D-Galacturonoyl) Amino Acids and Dipeptides
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## Abstract D‐Galacturonic acid derivatives, amide‐linked to amino acids or dipeptides, have been synthesized. These glycoconjugates exhibit stability when the uronic acid residue is protected with isopropylidene and acetyl groups or is in its pyranoside form. The formation of the amide or peptide