N-Glycyl-β-glycopyranosylamines, derivatives of mono- and disaccharides, and their use for the preparation of carboxylic acid glycoconjugates

被引：15

作者：

Likhosherstov, LM ^{[1
]}

Novikova, OS ^{[1
]}

Zheltova, AO ^{[1
]}

Shibaev, VN ^{[1
]}

机构：

[1] ND Zelinskii Organ Chem Inst, Moscow 117913, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2000年 / 49卷 / 08期

关键词：

glycoconjugates; carboxylic acids; N-chloroacetylglycosylamines; N-glycylglycosylamines;

D O I：

10.1007/BF02495096

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient preparative procedure was developed for the synthesis of N-glycyl-beta-glycopyranosylamines. derivatives of monosaccharides (D-galactose, D-mannose, L-fucose, and N-acetyl-D-glucosamine) and disaccharides (lactose, melibiose, cellobiose, and maltose). These compounds were demonstrated to be useful for the preparation of glycoconjugates of biologically active compounds containing the carboxy group (nicotinic, orotic, kynurenic, and indoleacetic acids). Synthetic pathways were developed for conversions of N-glycyl-beta-glycopyranosylamines into derivatives containing the carboxy group with the use of malonic and L-tartaric acid derivatives.

引用

页码：1454 / 1459

页数：6

共 25 条

[1] N-glycyl-β-glycopyranosylamines, derivatives of mono- and disaccharides, and their use for the preparation of carboxylic acid glycoconjugates
L. M. Likhosherstov
O. S. Novikova
A. O. Zheltova
V. N. Shibaev
Russian Chemical Bulletin, 2000, 49 : 1454 - 1459
[2] Synthesis of N-glycyl-β-glycopyranosylamines, human milk fucooligosaccharide derivatives
L. M. Likhosherstov
O. S. Novikova
I. A. Yamskov
V. E. Piskarev
Russian Chemical Bulletin, 2012, 61 : 1816 - 1821
[3] An improved procedure for the synthesis of N-bromoacetyl-β-glycopyranosylamines, derivatives of mono- and disaccharides
Likhosherstov, LM
Novikova, OS
Zheltova, AO
Shibaev, VN
RUSSIAN CHEMICAL BULLETIN, 2004, 53 (03) : 709 - 713
[4] Synthesis of N-glycyl-β-glycopyranosylamines, human milk fucooligosaccharide derivatives
Likhosherstov, L. M.
Novikova, O. S.
Yamskov, I. A.
Piskarev, V. E.
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (09) : 1816 - 1821
[5] An improved procedure for the synthesis of N-bromoacetyl-β-glycopyranosylamines, derivatives of mono- and disaccharides
L. M. Likhosherstov
O. S. Novikova
A. O. Zheltova
V. N. Shibaev
Russian Chemical Bulletin, 2004, 53 : 709 - 713
[6] Synthesis of N-glycyl-β-glycopyranosylamines, derivatives of main human secreted oligosaccharide core structures
Likhosherstov, L. M.
Novikova, O. S.
Kolotyrkina, A. N. G.
Piskarev, V. E.
RUSSIAN CHEMICAL BULLETIN, 2019, 68 (02) : 411 - 415
[7] Synthesis of N-glycyl-β-glycopyranosylamines, derivatives of main human secreted oligosaccharide core structures
L. M. Likhosherstov
O. S. Novikova
N. G. Kolotyrkina
V. E. Piskarev
Russian Chemical Bulletin, 2019, 68 : 411 - 415
[8] Curing and glass transition of epoxy resins from ester-carboxylic acid derivatives of mono- and disaccharides, and alcoholysis lignin
Hirose, S
Hatakeyama, T
Hatakeyama, H
MACROMOLECULAR SYMPOSIA, 2005, 224 : 343 - 353
[9] A new efficient synthesis of β-glycosylmines, derivatives of mono- and disaccharides with the use of ammonium carbamate
Likhosherstov, L.M.
Novikova, O.S.
Shibaev, V.N.
Doklady Akademii Nauk, 2002, 383 (04) : 500 - 504
[10] N-ACYLTETRAZOLE AS AN INTERMEDIATE FOR PREPARATION OF CARBOXYLIC-ACID DERIVATIVES
JURSIC, BS
SYNTHETIC COMMUNICATIONS, 1993, 23 (03) : 361 - 364

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