Synthesis of protected α-alkyl lanthionine derivatives

被引：8

作者：

Denoel, Thibaut ^{[1
]}

Zervosen, Astrid ^{[1
]}

Lemaire, Christian ^{[1
]}

Plenevaux, Alain ^{[1
]}

Luxen, Andre ^{[1
]}

机构：

[1] Univ Liege, Cyclotron Res Ctr, B-4000 Liege, Belgium

来源：

TETRAHEDRON | 2014年 / 70卷 / 30期

关键词：

Lanthionine; Sulfamidate; alpha-Alkyl amino acid; Peptidoglycan; Protected amino acid; ALPHA; ALPHA-DISUBSTITUTED AMINO-ACID; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT; CHEMISTRY;

D O I：

10.1016/j.tet.2014.05.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Protected alpha-alkyl lanthionine derivatives were synthesized in five steps starting from a known phenyl-oxazoline precursor. This approach involved the synthesis of a family of substituted cyclic sulfamidates and their regioselective opening by nucleophilic attack with a protected cysteine. This efficient multistep strategy affords various alpha-alkylated lanthionine derivatives in high yields. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：4526 / 4533

页数：8

共 50 条

[21] SYNTHESIS OF HYDRAZINE AND ITS ALKYL DERIVATIVES
OHME, R
ZUBEK, A
ZEITSCHRIFT FUR CHEMIE, 1968, 8 (02): : 41 - &
[22] Synthesis and Structure of Alkyl Derivatives of Convolvine
Kadirova, D. B.
Turgunov, K. K.
Tashkhodzhaev, B.
Aripova, S. F.
CHEMISTRY OF NATURAL COMPOUNDS, 2023, 59 (01) : 119 - 123
[23] Synthesis of corannulene and alkyl derivatives of corannulene
Seiders, TJ
Elliott, EL
Grube, GH
Siegel, JS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (34) : 7804 - 7813
[24] Synthesis and Structure of Alkyl Derivatives of Convolvine
D. B. Kadirova
K. K. Turgunov
B. Tashkhodzhaev
S. F. Aripova
Chemistry of Natural Compounds, 2023, 59 : 119 - 123
[25] Synthesis of fluorescent alkyl lactoside derivatives
Watanabe, Soichiro
CARBOHYDRATE RESEARCH, 2008, 343 (13) : 2325 - 2328
[26] Synthesis of lanthionine analogs of conotoxins
de Araujo, A. D.
Alewood, P. F.
JOURNAL OF PEPTIDE SCIENCE, 2006, 12 : 210 - 210
[27] Chemoselective synthesis of protected polyamines and facile synthesis of polyamine derivatives using O-alkyl-O′-(N-succinimidyl) carbonates
Adamczyk, M
Fishpaugh, JR
Heuser, KJ
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1998, 30 (03) : 339 - 348
[28] A NEW SYNTHESIS OF CYSTINE AND LANTHIONINE
ATKINSON, RO
POPPELSDORF, F
WILLIAMS, G
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (FEB): : 580 - 581
[29] Easy access to orthogonally protected α-alkyl aspartic acid and α-alkyl asparagine derivatives by controlled opening of β-lactams
Gerona-Navarro, G
García-López, MT
González-Muñiz, R
TETRAHEDRON LETTERS, 2003, 44 (32) : 6145 - 6148
[30] A flexible approach for the asymmetric synthesis of N-protected (R)-5-alkyl tetramates and (R)-5-alkyl tetramic acid derivatives
Huang, PQ
Deng, J
SYNLETT, 2004, (02) : 247 - 250

← 1 2 3 4 5 →