A new synthetic method for α- and β-glycosyl ureas and its application to the synthesis of glycopeptide mimics with urea-glycosyl bonds

被引：1

作者：

Ichikawa, Y ^{[1
]}

Nishiyama, T ^{[1
]}

Isobe, M ^{[1
]}

机构：

[1] Nagoya Univ, Sch Bioagr Sci, Organ Chem Lab, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

SYNLETT | 2000年 / 09期

关键词：

amines; azides; carbohydrate; glycosyl isocyanate; urea;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new procedure for the stereospecific synthesis of alpha- and beta -glycosyl isocyanates by oxidation of glycosyl isocyanides has been developed. The reaction of alpha- and beta -glucosyl isocyanates with amines proceeds smoothly to provide alpha- and beta -glucosyl ureas with a net retention of the stereochemistry at the anomeric position. This method offers the synthesis of a building block for the glycopeptide mimics with urea-glycosyl linkages.

引用

页码：1253 / 1256

页数：4

共 50 条

[41] A new method for the generation of azoalkenes from ketohydrazones and its application to the synthesis of tetrahydropyridazine derivatives
Gaonkar, SL
Rai, KML
TETRAHEDRON LETTERS, 2005, 46 (35) : 5969 - 5970
[42] A new method for generation of magnesium carbenoids and magnesium carbanions, and its application to organic synthesis
Satoh, T
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2003, 61 (02) : 98 - 110
[43] NEW METHOD FOR AN EPOXIDATION OF OLEFINS AND ITS APPLICATION TO A BIOMIMETIC TYPE SYNTHESIS OF MONOTERPENES, LINALYLOXIDES
KAMETANI, T
NEMOTO, H
FUKUMOTO, K
HETEROCYCLES, 1977, 6 (9-10) : 1365 - 1370
[44] A New Preparation Method of Bimodal Catalyst Support and Its Application in Fischer–Tropsch Synthesis
Yi Zhang
Yoshiharu Yoneyama
Kaoru Fujimoto
Noritatsu Tsubaki
Topics in Catalysis, 2003, 26 : 129 - 137
[45] Development of new synthetic methods and its application to total synthesis of nitrogen-containing bioactive natural products
Kibayashi, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (11) : 1375 - 1386
[46] A convenient new method to construct 1-alkynyl cyclopropanol and its synthetic application to prepare trisubstituted dienones
An, Yan
Liu, Jie
Jiang, Hai-Ying
Wang, Yahui
Chen, Zili
TETRAHEDRON LETTERS, 2008, 49 (19) : 3124 - 3128
[47] A NEW SYNTHESIS OF ARYL-ALIPHATIC ALCOHOLS .3. APPLICATION OF THE METHOD TO SOME NATURAL AND SYNTHETIC COMPOUNDS
DRUKKER, EA
BEETS, MGJ
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1951, 70 (01): : 29 - 34
[48] A new one-pot method for the synthesis of α-siloxyamides from aldehydes or ketones and its application to the synthesis of (-)-bestatin
Nemoto, H
Ma, RJ
Suzuki, I
Shibuya, M
ORGANIC LETTERS, 2000, 2 (26) : 4245 - 4247
[49] Synthesis of a new glycosyl-acceptor derivative of normuramic acid lactam and its use for the preparation of a spacer-armed disaccharide structurally similar to the repeating fragment of the bacterial spore cell wall peptidoglycan
Pertel, S. S.
Kakayan, E. S.
Zinin, A. I.
Kononov, L. O.
RUSSIAN CHEMICAL BULLETIN, 2024, 73 (12) : 3722 - 3731
[50] The Paterno-Buchi reaction of N-acyl enamines and aldehydes -: The development of a new synthetic method and its application to total synthesis and molecular recognition studies
Bach, T
SYNLETT, 2000, (12) : 1699 - 1707

← 1 2 3 4 5 →