175977-99-8Relevant academic research and scientific papers
Guanidine/guanidinium nitrate; a mild and selective O-deacetylation reagent that leaves the N-Troc group intact
Ellervik, Ulf,Magnusson, Goeran
, p. 1627 - 1628 (1997)
Treatment of O-acetyl-protected sugars with a methanolic solution of guanidine/guanidinium nitrate caused the removal of the acetyl groups (91-99% isolated yield), without affecting other protecting groups. Removal of O-benzoyl groups required a longer re
Convergent Synthesis of Sialyl LewisX- O-Core-1 Threonine
Sardar, Mohammed Y. R.,Mandhapati, Appi Reddy,Park, Simon,Wever, Walter J.,Cummings, Richard D.,Chaikof, Elliot L.
, p. 4963 - 4972 (2018/05/17)
Selectins are a class of cell adhesion molecules that play a critical role during the initial steps of inflammation. The N-terminal domain of P-selectin glycoprotein ligand-1 (PSGL-1) binds to all selectins, but with the highest affinity to P-selectin. Re
Synthesis of LewisX-O-Core-1 threonine: A building block for O-linked LewisX glycopeptides
Sardar, Mohammed Y.R.,Krishnamurthy, Venkata R.,Park, Simon,Mandhapati, Appi Reddy,Wever, Walter J.,Park, Dayoung,Cummings, Richard D.,Chaikof, Elliot L.
, p. 47 - 53 (2017/10/27)
LewisX (LeX) is a branched trisaccharide Galβ1→4(Fucα1→3)GlcNAc that is expressed on many cell surface glycoproteins and plays critical roles in innate and adaptive immune responses. However, efficient synthesis of glycopeptides bearing LeX remains a major limitation for structure-function studies of the LeX determinant. Here we report a total synthesis of a LeX pentasaccharide 1 using a regioselective 1-benzenesulfinyl piperidine/triflic anhydride promoted [3 + 2] glycosylation. The presence of an Fmoc-threonine amino acid facilitates incorporation of the pentasaccharide in solid phase peptide synthesis, providing a route to diverse O-linked LeX glycopeptides. The described approach is broadly applicable to the synthesis of a variety of complex glycopeptides containing O-linked LeX or sialyl LewisX (sLeX).
A high yielding chemical synthesis of sialyl Lewis x tetrasaccharide and Lewis x trisaccharide; examples of regio- and stereodifferentiated glycosylations
Ellervik, Ulf,Magnusson, Goeran
, p. 9314 - 9322 (2007/10/03)
Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D- glucopyranoside (8) with the donor phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1- thio-β-D-galactopyranoside (11) gave the lactosamine derivative 14, which was fucosylated with the donor 15 to give the Le(x) trisaccharide glycoside 2 after deprotection. Regioselective sialylation of the partially protected Le(x) trisaccharide triol 24 with the sialyl donor 25 gave, after deprotection, the SLe(x) tetrasaccharide glycoside 1. The overall yields of 2 and 1 from the monosaccharide starting materials 8, 11, 15, and 25 were 56% and 29%, respectively. In contrast to the virtually complete regio- and stereoselective galactosylation of 8, fucosylation with the benzyl-protected donor 15 gave the corresponding 1→3- and 1→4-linked disaccharides in a ratio of 3.6:1 (highly stereo- but not regioselective glycosylation), whereas fucosylation with acetyl-protected donor 18 gave a 2.2:1 β/α-mixture of 4- O-linked disaccharides (highly regio- but not stereoselective glycosylation).
Borane/Bu2BOTf: A mild reagent for the regioselective reductive ring opening of benzylidene acetals in carbohydrates
Jiang, Lu,Chan, Tak-Hang
, p. 355 - 358 (2007/10/03)
BH3/Bu2OTf is an effective reagent to reductively cleave 4,6-O-benzylidene acetals of various hexopyranosides to the corresponding 4-O-benzyl ethers. 4,6-O-Isopropylidene acetals can be similarly cleaved. Common protecting groups are
Total synthesis of VIM-2 ganglioside isolated from human chronic myelogenous leukemia cells
Ehara, Taro,Kameyama, Akihiko,Yamada, Yutaka,Ishida, Hideharu,Kiso, Makoto,Hasegawa, Akira
, p. 237 - 252 (2007/10/03)
A total synthesis of the tumor-associated glycolipid antigen, VIM-2. is described. Phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1 → 4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (7), a key intermediate prepared by condensation of phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (6) and 2,3,4-tri-O-benzoyl-6-O-benzyl-α-D-galactopyranosyl bromide (5), was glycosylated with methyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (8) to give the trisaccharide donor 9, which, on coupling with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1 → 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (10), afforded the pentasaccharide 11. The regioselective glycosylation of 12 (derived by O-debenzoylation of 11) with 7 gave the heptasaccharide 13, which was converted by treatment with hydrazine monohydrate and subsequent N-acetylation into the hexasaccharide acceptor 14. The stereo- and regio-selective glycosylation of 14 with methyl (phenyl 5-acetamido-4,7,8,9-O-benzoyl-3,5-dideoxy-2-thio-D-glycero-β-D-galact o-2-nonulopyranosid)onate (16) gave the desired octasaccharide 18. Hydrogenolytic removal of the benzyl groups in 18 and successive O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile gave the α-trichloroacetimidate 21, which was then coupled with (2S,3R,4E)-2-azido-3-O-(tert-butyldiphenylsilyl)4-octadecene-1,3-diol (22) to give 23. Compound 23 was transformed, via selective reduction of the azido group, N-introduction of octadecanoic acid, O-desilylation, O-deacylation, and saponification of the methyl ester group, into the title VIM-2 ganglioside 26.
