26531-91-9Relevant 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.
Acetalation studies. Part VI. Concerning the effects of ultrasound on the benzylidenation of some alkyl D-glycopyranosides
Chittenden, Gordon J. F.
, p. 607 - 609 (2007/10/02)
The effects of ultrasound on conventional Freudenberg-type benzylidenation reactions of some alkyl D-glycopyranosides is described.A considerable enhancement in the rates of formation of the expected acetals was observed.The pure products were obtained in good yields.Some of the crude air-dried products were suitable for direct derivatisation.
