The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in syntheses of hyaluronic acid-related tetra-, hexa-, and octa-saccharides having a methyl beta-D-glucopyranosiduronic acid at the reducing end
The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in syntheses of hyaluronic acid-related tetra-, hexa-, and octa-saccharides having a methyl beta-D-glucopyranosiduronic acid at the reducing end
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DOI：
10.1016/0008-6215(96)00085-7
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发表时间：
1996-07-19
影响因子：
3.1
通讯作者：
Jacquinet, JC
中科院分区：
文献类型：
--
作者：
Blatter, G;Jacquinet, JC
Expeditious and stereocontrolled syntheses are reported of beta-D-Glc pNAc-(1 --> 4)-[beta-D-Glc pA-(1 --> 3)-beta-D-Glc pNAc-(1 --> 4)](n)-beta-D-Glc pA-(1 --> OMe), where n = 1, 2, and 3, which represent structural elements of the extracellular polysaccharide hyaluronic acid. Condensation of 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamide-alpha-D-glucopyranosyl trichloroacetimidate with methyl (4-methoxyphenyl 2,3-di-O-benzoyl-beta-D-glucopyranosid)uronate gave the disaccharide derivative 9, which was demethoxyphenylated and imidoylated to afford the pivotal disaccharide trichloroacetimidate 7. Condensation of 7 with methanol followed by O-dechloroacetylation gave the acceptor 8. Coupling of 7 with 8 gave the tetrasaccharide derivative 4. O-Dechloroacetylation of 4 followed by condensation with imidate 7 afforded hexasaccharide 5, which was transformed into octasaccharide 6 by a similar two-step procedure. Subsequent O-dechloroacetylation, transformation of the N-trichloroacetyl groups into N-acetyl, debenzylidenation, and saponification of 4-6 afforded the tetra- (1), hexa- (2), and octa-saccharide (3) derivatives in high yields, as their sodium salts. (C) 1996 Elsevier Science Ltd.
