Synthesis of Glycosides with 4-(4-Hydroxyphenyl)-1,2,3-thia- and -selenadiazole Aglycones

被引：3

作者：

Pevzner, L. M. ^{[1
]}

Petrov, M. L. ^{[1
]}

Erkhitueva, E. B. ^{[2
]}

Polukeev, V. A. ^{[3
]}

Stepakov, A. V. ^{[2
]}

机构：

[1] St Petersburg State Inst Technol Tech Univ, Moskovskii Pr 26, St Petersburg 190013, Russia

[2] St Petersburg State Univ, St Petersburg, Russia

[3] Inst Expt Med, St Petersburg, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2019年 / 89卷 / 07期

关键词：

glycosylation; Konnigs-Knorr reaction; interphase catalysis; 1; 2; 3-thiadiazoles; semicarbazides; 3-selenadiazoles; BETA-D-GLUCOPYRANOSIDES;

D O I：

10.1134/S1070363219070089

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Glycosylation of 4-(4-hydroxyphenyl)-1,2,3-thia(selena)diazoles with 1-alpha-bromo-2,3,4,6-tetra-O-acetyl-D-glucopyranose, 1-alpha-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose, and 1-alpha-bromo-2,3,5-tri-O-acetyl-D-xylopyranose under the conditions of interphase catalysis has afforded the corresponding acetylated glycosides. An alternative pathway of selenadiasole glycosides synthesis from semicarbazones of 1-beta-O-(4-acetylphenyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose, -2,3,4,6-tetra-O-acetyl-D-galactopyranose, and -2,3,5-tri-O-acetyl-D-xylopyranose via oxidation with selenium dioxide has been elaborated.

引用

页码：1398 / 1405

页数：8

共 50 条

[41] Synthesis and study of cobalt(II), nickel(II), and copper(II) complexes with 4-(4-hydroxyphenyl)-1,2,4-triazole
E. V. Lider
E. V. Peresypkina
L. G. Lavrenova
L. A. Sheludyakova
A. I. Smolentsev
T. I. Yaroshenko
V. N. Elokhina
Russian Journal of Coordination Chemistry, 2012, 38 : 353 - 362
[42] Electrochemical Synthesis Based on the Oxidation of 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone in the Presence of Nucleophiles
Amani, Amene
Nematollahi, Davood
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24): : 11302 - 11306
[43] 4-(4-chlorophenyl)-5-[2-methyl-1-(4methylphenyl)-2-nitropropyl]-1,2,3selenadiazole
Gunasekaran, B.
Manivannan, V.
Saravanan, S.
Muthusubramanian, S.
Nethaji, M.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O4024 - U2810
[44] 2-(4-HYDROXYPHENYL)BENZOTHIAZOLE
TEO, SB
OKECHUCKWU, RC
TEOH, SG
FUN, HK
CHINNAKALI, K
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 (pt 8) : 1629 - 1630
[45] 4-(4-chlorophenyl)-5-[1-(4-chlorophenyl)-2-methyl-2-nitropropyl]-1,2,3-selenadiazole
Marx, A.
Saravanan, S.
Muthusubramanian, S.
Manivannan, V.
Rath, Nigam P.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O349 - U1521
[46] SYNTHESIS OF 4-(AMINOMETHYL)-1-THIA-2-SELENA-CYCLOPENTANE
BERGSON, G
ARKIV FOR KEMI, 1962, 19 (01): : 75 - &
[47] Synthesis and synthetic applications of (4-hydroxyphenyl) perfluoroalkylmethanols
Terashima, Kyu
Kawasaki-Takasuka, Tomoko
Minami, Ichiro
Yamazaki, Takashi
TETRAHEDRON, 2022, 104
[48] Hexaaquacadmium(II) bis{4-[2-(4-hydroxyphenyl)-2-propyl]phenolate} dihydrate
Fu, AY
Wang, DQ
Sun, YL
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : M2353 - M2354
[49] 4-(4-HYDROXYPHENYL)-2-BUTANONE (RASPBERRY KETONE) - REVIEW OF NATURAL OCCURRENCE AND BIOGENESIS
DEIFEL, A
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1989, 188 (04): : 330 - 332
[50] (E)-3-[4-(Decyloxy)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
Razak, Ibrahim Abdul
Fun, Hoong-Kun
Ngaini, Zainab
Rahman, Norashikin Irdawaty Abd
Hussain, Hasnain
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1092 - U2676

← 1 2 3 4 5 →