Dimerization of propargyl and homopropargyl 6-azido- 6-deoxy- glycosides upon 1,3-dipolar cycloaddition

• Nikolas Pietrzik,
• Daniel Schmollinger and
• Thomas Ziegler

Beilstein J. Org. Chem. 2008, 4, No. 30, doi:10.3762/bjoc.4.30

• , affording the dimeric glycoside 7a beside products of oligomerization (Scheme 1). The reaction proceeded significantly slower than the coupling of 4a and 5. A faster reaction occurred upon irradiation with microwave, which also gave a higher yield (54%) of 7a. Benzoylated glycoside 4a' did not give any

• compounds on TLC (ethyl acetate/n-hexane 1:1) and appeared to be products of oligomerization of the starting material 4. In the case of benzoylated glycoside 4a' where no cyclic dimer could be isolated from the complex reaction mixture, FAB MS of the purified mixture indeed revealed the presence of linear

Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells

• Li-Rong Sun,
• Chen Qing,
• Yan-Li Zhang,
• Shu-Yu Jia,
• Zhong-Rong Li,
• Shen-Ji Pei,
• Ming-Hua Qiu,
• Michael L. Gross and
• Samuel X. Qiu

Beilstein J. Org. Chem. 2007, 3, No. 3, doi:10.1186/1860-5397-3-3

• , the sugar moiety must be either a-L-arabinopyranosyl-[4C1 chair conformation) or β-D-arabinopyranosyl [1C4 chair conformation], with the former being more favorable, as it is a common component of the triterpene glycoside isolated from Cimicifuga plants, whereas the isolation of the latter has not

Investigation of acetyl migrations in furanosides

• O. P. Chevallier and
• M. E. Migaud

Beilstein J. Org. Chem. 2006, 2, No. 14, doi:10.1186/1860-5397-2-14

• acetyl moieties. Such direct transesterification is intermolecular and while it has been observed in nucleoside-phosphoramidite and glycoside chemistry,[20][21][22][23] this alkoxide-promoted intermolecular acetyl migration process has been overlooked in furanosides. The isolated quantities of 1c and 1d

Study of thioglycosylation in ionic liquids

• Jianguo Zhang and
• Arthur Ragauskas

Beilstein J. Org. Chem. 2006, 2, No. 12, doi:10.1186/1860-5397-2-12

• ionic liquids for the synthesis of alkyl glycoside and disaccharides via coupling of thioalkyl glycosyl donors with glycal acceptors. Alkyl glycosides and oligosaccharides are important intermediates and products in the synthesis of biologically active natural compounds and mimics. For example, tetra-O

• -acetyl-glycoside derivatives have been used in the synthesis of glycosyltransferase inhibitors and clearing agents to enhance anti-tumor activities.[10][11] In addition, alkyl glycosides possessing long alkyl chain have gained wide interest as non-ionic surfactants.[12] A variety of reagents have been

• reported to promote the formation of a glycoside bond which include, classical glycosyl halides, thioglycosides, pentenyl glycosides, anomeric trichloroacetimidates and others.[13] As reviewed by Oscarson,[14] thioalkyl or thioaryl glycosyl donors have been shown to exhibit excellent selectivity and

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• protonated, and the corresponding ammonium ions mimick the charge of the presumed transition states or intermediates of the enzymatic glycoside hydrolyses [18]. More recently, attention has been increasingly accorded to seven- and eight-membered ring systems [19][20][21][22][23][24][25][26][27][28][29][30