138857-75-7Relevant academic research and scientific papers
Synthesis of 5-aminopentyl 4,6-O--β-D-galactopyranoside and its use as a ligand for the affinity chromatography of human serum amyloid P protein
Ziegler, Thomas,Eckhardt, Elisabeth,Strayle, Jochen,Herzog, Helmut
, p. 167 - 184 (2007/10/02)
A series of 2,3-di-O-benzoyl-D-galctopyranosides, α-allyl (5), α-benzyl (6), β-ethyl-1-thio (7), β-phenyl-1-thio (8), and α-methyl (9), were prepared from the corresponding 4,6-O-benzylidene derivatives and were acetalated in acetonitrile with methyl pyruvate, to give diastereoselectively the 2,3-di-O-benzoyl-4,6-O--D-galactopyranosides 10-16.The latter were converted into the 2,3-di-O-benzoyl-4,6-O--D-galactopyranosyl α- and β-trichloroacetimidates 19 and 20, α- and β-fluorides 21 and 22, the α-bromide 23, and the α-chloride 24, respectively.These donors, including the phenyl 1-thiogalactoside 14, reacted with 5-pentanol to give the corresponding protected β-D-galactoside 27, deblocking of which afforded the title compound 1.Binding of 1 to epoxypropyl-modified acrylamide beads gave an affinity adsorbent that was used to isolate serum amyloid P protein from human serum.
Convenient synthesis of 4,6-O-pyruvate acetal containing glycosides via tetraisopropyldisiloxanediyl protected sugars
Ziegler,Eckhardt,Neumann,Birault
, p. 1013 - 1017 (2007/10/02)
Treatment of alkyl D-glycopyranosides and alkyl or phenyl 1-thio-β-D-glycopyranosides 1 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane gave the corresponding 4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) protected glycosides 2 which were subsequen
Lewis Acid-Catalysed Anomerisation and Rearrangement of Alkyl D-Glycopyranosides During Acetalisation with Methyl Pyruvate: How to Utilise it for the Preparation of 1-(Carboxyethylidene)glycopyranosyl Donors
Ziegler, Thomas,Eckhardt, Elisabeth,Herold, Gerhard
, p. 441 - 452 (2007/10/02)
The preparation of 4,6-O-(1-methoxycarbonylethylidene)-D-glycopyranosides 5 starting from 2,3-di-O-benzoyl-D-glycopyranosides 1 and their 4,6-bis-O-trimethylsilyl ethers 2 using methyl 2,2-bis(phenylthio)propionate (4) and methyl pyruvate (3), respectivel
Diastereoselective formation of pyruvylated glycosides from partly protected sugars and methyl pyruvate
Ziegler,Eckhardt,Herold
, p. 4413 - 4416 (2007/10/02)
Various partly protected sugars (gluco-, manno-, and galactopyranosides) were acetalized with methyl pyruvate in moderate to good yield with BF3-etherate as the condensing reagent. Thus, (1-methoxycarbonyl)ethylidene glycosides were obtained di
