Synthesis and NMR elucidation of four novel 2-(trimethylsilyl)ethyl glycosides

被引：2

作者：

Qu, Huanhuan ^{[1
,2
]}

Sun, Wenji ^{[2
]}

Zhang, Yanyan ^{[1
]}

Sollogoub, Matthieu ^{[1
]}

Zhang, Yongmin ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, Inst Parisien Chim Mol, UMR 7201, F-75005 Paris, France

[2] NW Univ Xian, Biomed Key Lab Shaanxi Prov, Xian 710069, Peoples R China

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2014年 / 40卷 / 04期

关键词：

Total synthesis; Structure elucidation; Glycosides; NMR spectroscopy; Oligosaccharides; CHEMICAL-SYNTHESIS; GLYCOSYLATION; OLIGOSACCHARIDES; TRANSFORMATION;

D O I：

10.1007/s11164-013-1060-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Four novel 2-(trimethylsilyl)ethyl glycosides have been synthesized by a short and efficient route starting from d-glucose. Their structures were elucidated by applying high-resolution mass spectra, and one-dimensional and two-dimensional NMR techniques. These glycosides were prepared and used as intermediate building blocks in the scheme developed for oligosaccharide construction.

引用

页码：1557 / 1564

页数：8

共 50 条

[21] SYNTHESIS, REACTIONS, AND INTERCONVERSIONS OF SOME 2-(TRIMETHYLSILYL)ETHYL SUBSTITUTED SULFUR-COMPOUNDS
SCHWAN, AL
BRILLON, D
DUFAULT, R
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (02): : 325 - 333
[22] 2-(TRIMETHYLSILYL)ETHYL ESTERS AS CARBOXYL PROTECTING GROUP - APPLICATION IN SYNTHESIS OF (-)-(S)-CURVULARIN
GERLACH, H
HELVETICA CHIMICA ACTA, 1977, 60 (08) : 3039 - 3044
[23] Structure elucidation and NMR spectral assignments of four neolignan glycosides from Osmanthus ilicifolius
Machida, Koichi
Sakamoto, Shigeaki
Kikuchi, Masao
MAGNETIC RESONANCE IN CHEMISTRY, 2008, 46 (10) : 990 - 994
[24] 2-(TRIMETHYLSILYL)ETHYL GLYCOSIDES .3. SYNTHESIS, ANOMERIC DEBLOCKING, AND TRANSFORMATION INTO 1,2-TRANS 1-O-ACYL SUGARS
JANSSON, K
AHLFORS, S
FREJD, T
KIHLBERG, J
MAGNUSSON, G
DAHMEN, J
NOORI, G
STENVALL, K
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24): : 5629 - 5647
[25] Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate
Lin, Wenhong
Meyer, Shea T.
Dormann, Shawn
Chisholm, John D.
ORGANICS, 2021, 2 (01): : 17 - 25
[26] SYNTHESIS OF 2-(TRIMETHYLSILYL)ETHYL BENZENESULFENATE AND BENZENESELENENATE AND THEIR REACTION WITH SOME ELECTROPHILES IN THE PRESENCE OF TETRABUTYLAMMONIUM FLUORIDE
OIDA, T
OHNISHI, A
SHIMAMAKI, T
HAYASHI, Y
TANIMOTO, S
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (02) : 702 - 704
[27] Synthesis of fluorinated allylic amines:: Reaction of 2-(trimethylsilyl)ethyl sulfones and sulfoxides with fluorinated imines
Fustero, Santos
Flores, Sonia
Cunat, Ana C.
Jimenez, Diego
del Pozo, Carlos
Bueno, Jorge
Sanz-Cervera, Juan F.
JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (10) : 1248 - 1254
[28] 2-(Trimethylsilyl)ethyl sulfoxides as a convenient source of sulfenate anions
Foucoin, Florian
Caupene, Caroline
Lohier, Jean-Francois
Santos, Jana Sopkova de Oliveira
Perrio, Stephane
Metzner, Patrick
SYNTHESIS-STUTTGART, 2007, 9 (09): : 1315 - 1324
[29] Entering the leinamycin rearrangement via 2-(trimethylsilyl)ethyl sulfoxides
Keerthi, Kripa
Gates, Kent S.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (10) : 1595 - 1600
[30] STRUCTURE OF 5-TRIMETHYLSILYL 2-[1,2,2-TRIS(TRIMETHYLSILYL) ETHYL] PHENOXYTRIMETHYLSILANE
COURSEILLE, C
LEROY, F
BIRAN, C
EFENDENE, B
DUNOGUES, J
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 : 386 - 388

← 1 2 3 4 5 →