583040-99-7Relevant articles and documents
Synthesis of spirostanol saponins via gold(I)-catalyzed glycosylation in the presence of Ga(OTf)3, In(OTf)3, or HOTf
Ehianeta, Teddy Stephen,Shen, Dacheng,Xu, Peng,Yu, Biao
supporting information, p. 827 - 833 (2019/07/22)
An effective approach relying on a Lewis acid- or Br?nsted acid-assisted gold(I)-catalyzed glycosylation has been reported in the synthesis of a panel of the representative natural spirostanol saponins, namely polyphyllin D (1), polyphyllin V (2), dioscin (3), formosanin C (4), and a derivative of polyphyllin D bearing a terminal azide group (5). This approach highlights the engagement of low loadings of Ph3AuPOTf (≤ 0.5 mol%) in the presence of Ga(OTf)3, In(OTf)3, or HOTf (~10mol%) as a co-catalyst, at practical reaction rates as an alternative to the conventional ~10 mol% loadings of the gold(I) catalyst in the glycosylation. Polyphyllin D (1) was obtained in 41% overall yield over six steps compared to the maximum 30% yield in previous syntheses where conventional donors and promoters were used. By exploiting a regioselective rhamnosylation, a “one-pot” approach was adopted to assemble 1 and 5, thus further strengthening the efficiency of the gold(I)-catalyzed glycosylation.
Organoiridium complexes: Efficient catalysts for the formation of sugar acetals and ketals
Mandal, Soumik,Verma, Prashant Ranjan,Mukhopadhyay, Balaram,Gupta, Parna
experimental part, p. 2007 - 2010 (2011/12/01)
[Cp*IrCl2]2 is used as an efficient promoter for the synthesis of sugar acetals and ketals with good to excellent yields. The catalyst is found to be general for a wide range of sugars.
Efficient synthesis of a 6-deoxytalose tetrasaccharide related to the antigenic O-polysaccharide produced by Aggregatibacter actinomycetemcomitans serotype c
Cai, Xiangyan,Zong, Guanghui,Xu, Yanjun,Zhang, Jianjun,Liang, Xiaomei,Wang, Daoquan
experimental part, p. 1230 - 1234 (2010/09/07)
Concise synthesis of a 6-deoxy-α-l-talose tetrasaccharide, 6-deoxy-α-l-Talp-(1→3)-6-deoxy-α-l-Talp-(1→2)-6-deoxy-α-l-Talp-(1→3)-6-deoxy-α-l-Talp, the dimer of the disaccharide repeating unit of the OPS from Aggregatibacter actinomycetemcomitans serotype c
Using biological performance similarity to inform disaccharide library design
Tanikawa, Tetsuya,Fridman, Micha,Zhu, Wenjiang,Faulk, Brian,Joseph, Isaac C.,et al.
supporting information; experimental part, p. 5075 - 5083 (2009/09/30)
Designing better small-molecule discovery libraries requires having methods to assess the consequences of different synthesis decisions on the biological performance of resulting library members. Since we are particularly interested in how stereochemistry
ANTIBODIES FOR THE DETECTION OF BACILLUS ANTHRACIS AND VACCINE AGAINST B. ANTHRACIS INFECTIONS
-
Page/Page column 20-21, (2008/06/13)
35 Abstract The present invention relates to conjugates of oligosaccharides of formula 1, wherein R is a linker to a carrier protein and optionally comprises up to three further saccharides, 5 and which are useful for vaccination, methods of synthesis of
Total synthesis of antigen Bacillus anthracis tetrasaccharide - Creation of an anthrax vaccine candidate
Werz, Daniel B.,Seeberger, Peter H.
, p. 6315 - 6318 (2007/10/03)
Fighting Anthrax by recognizing its coat: The spores of Bacillus anthracis bear unique oligosaccharides on their surface for interaction with a host. These specific oligosaccharides may prove useful in the development of vaccines against this major biowar
Synthesis of the trisaccharide repeating unit of the O-antigen related to the enterohemorrhagic Escherichia coli type O26:H
Sarkar, Kakali,Mukherjee, Indrani,Roy, Nirmolendu
, p. 95 - 107 (2007/10/03)
L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharid