161007-95-0Relevant articles and documents
Boronic acid-catalyzed final-stage site-selective acylation for the total syntheses of O-3′-acyl bisabolol β-D-fucopyranoside natural products and their analogues
Nakamura, Yuki,Ochiai, Takayuki,Makino, Kazuishi,Shimada, Naoyuki
, p. 281 - 285 (2021/03/08)
The first concise total syntheses of O-3′-senecioyl α-bisabolol β-D-fucopyranoside (4a) and O-3′isovaleroyl α-bisabolol β-D-fucopyranoside (4b) were achieved through final-stage site-selective acylation via the activation of cis-vicinal diols by imidazole
SULFATED-GLYCOLIPIDS AS ADJUVANTS FOR VACCINES
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Page/Page column 31; 38, (2016/01/25)
A synthetic charged glycolipid is described comprising a sulfated saccharide group covalently linked to the tree sn-1 hydroxyl group of the glycerol backbone of an archaeal core lipid via a beta linkage. The synthetic charged glycolipids include compounds
Synthesis and evaluation of four hederagenin glycosides as α-glucosidase inhibitor
Liu, Qing-Chao,Guo, Tian-Tian,Guo, Shou-Dong,Li, Wen-Hong,Li, Dong
, p. 142 - 149 (2013/03/14)
The four hederagenin glycosides 1-4 were efficiently synthesized through one-pot sequential glycosylations with glycose 1-(trichloroacetimidate)s as donors, resulting in a significantly simplified synthetic procedure without isolation of glycosylation intermediates. The activity of the synthetic hederagenin glycosides 1-4 against α-glucosidase type IV was evaluated; hederagenin glycoside 4 containing an α-L-rhamnopyranosyl unit showed the best activity with an IC50 value of 47.9 μM. Copyright
Total synthesis of ouabagenin and ouabain
Reddy, Maddi Sridhar,Zhang, Hongxing,Phoenix, Serge,Deslongchamps, Pierre
supporting information; experimental part, p. 725 - 741 (2011/06/25)
A full account of the total synthesis of ouabagenin and ouabain is described. A highly stereocontrolled anionic cycloaddition for the rapid construction of the basic steroid skeleton is a pivotal conversion for the whole strategy. A careful study was need
Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues
Piochon, Marianne,Legault, Jean,Gauthier, Charles,Pichette, Andre
experimental part, p. 228 - 236 (2009/09/05)
α-Bisabolol β-d-fucopyranoside, a cytotoxic naturally occurring compound, was efficiently synthesized along with five other α-bisabolol glycosides (β-d-glucoside, β-d-galactoside, α-d-mannoside, β-d-xyloside and α-l-rhamnoside). Glycosidation of α-bisabol
Total synthesis of ouabagenin and ouabain
Zhang, Hongxing,Sridhar Reddy, Maddi,Phoenix, Serge,Deslongchamps, Pierre
, p. 1272 - 1275 (2008/12/22)
(Chemical Equation Presented) The highly oxygenated steroid ouabagenin (1b) and its glycoside ouabain (1a) were prepared by a strategy based on a polyanionic cyclization. Starting building blocks A and B were combined to give the key intermediate C and transformed into 1b in 27 steps. Finally, ouabagenin (1b) was converted into ouabain (1a) in six steps (see scheme).
Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents
Gauthier, Charles,Legault, Jean,Lebrun, Maxime,Dufour, Philippe,Pichette, Andre
, p. 6713 - 6725 (2007/10/03)
The weak hydrosolubility of betulinic acid (3) hampers the clinical development of this natural anticancer agent. In order to circumvent this problem and to enhance the pharmacological properties of betulinic acid (3) and the lupane-type triterpenes lupeol (1), betulin (2), and methyl betulinate (7), glycosides (β-d-glucosides, α-l-rhamnosides, and α-d-arabinosides) were synthesized and in vitro tested for cytotoxicity against three cancerous (A-549, DLD-1, and B16-F1) and one healthy (WS1) cell lines. The addition of a sugar moiety at the C-3 or C-28 position of betulin (2) resulted in a loss of cytotoxicity. In contrast, the 3-O-β-d-glucosidation of lupeol (1) improved the activity by 7- to 12-fold (IC50 14-15.0 μM). Moreover, the results showed that cancer cell lines are 8- to 12-fold more sensitive to the 3-O-α-l-rhamnopyranoside derivative of betulinic acid (IC50 2.6-3.9 μM, 22) than the healthy cells (IC50 31 μM). Thus, this study indicates that 3-O-glycosides of lupane-type triterpenoids represent an interesting class of potent in vitro cytotoxic agents.
Practical synthesis of a tetrasaccharide derivative corresponding to ristomycin A and ristocetin A
Zhang, Meimei,Du, Yuguo,Kong, Fanzuo
, p. 319 - 324 (2007/10/03)
A practical synthesis of fully benzoylated tetrasaccharide, whose free form is indispensable to the antibiotic ristomycin A for the process of dimerization and binding to the cell wall, was achieved via sequential assembly of the building blocks, allyl 3,4-di-O-benzoyl-α-D-glucopyranoside, 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate, 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate, and 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl trichloroacetimidate. A one-pot preparation of allyl 3,4-di-O-benzoyl-2-O-tert-butyldimethylsilyl-6-O-triphenylmethyl-α-D- glucopyranoside is described, and regioselective glycosylation is carried out using perbenzoylated sugar trichloroacetimidates as glycosyl donors in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf).
Synthesis of a tri- and tetrasaccharide fragment specific for the Shigella flexneri serotype 5a O-antigen. A reinvestigation
Mulard, Laurence A.,Ughetto-Monfrin, Joel
, p. 721 - 753 (2007/10/03)
Stereocontrolled, stepwise synthesis of methyl α-L-rhamnopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranoside (A(E)B, 1) and methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl -(1→2)-[α-D-glucopyranosyl-(1 →3)]-α-L-rhamnopy
Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof
Ziegler, Thomas,Bien, Frank,Jurisch, Claus
, p. 765 - 780 (2007/10/03)
The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1- O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting part