One‐Pot Catalytic Glycosidation/Fmoc Removal – An Iterable Sequence for Straightforward Assembly of Oligosaccharides Related to HIV gp120

Abstract

The removal of a transient Fmoc protecting group can be simply performed by the addition of excess Et3N just after the accomplishment of a Bi(OTf)3‐promoted glycosidation reaction. The obtained oligosaccharide can be directly employed as a glycosyl acceptor for further elongation of the saccharide. The preparation of biologically important, linear and branched mannans incorporated into HIV gp120 demonstrates that the iteration of this one‐pot sequence leads to a very straightforward oligosaccharide assembly.

A Concise Synthesis of a BODIPY-Labeled Tetrasaccharide Related to the Antitumor PI-88

“…Several synthetic approaches to analogues of tetra- and pentasaccharides 1 have already been reported [ 22 , 23 , 24 , 25 , 26 , 27 , 28 ]. In those approaches, different types glycosyl donors have been employed.…”

Rapid assembly of gp120 oligosaccharide moieties via one-pot glycosidation–deprotection sequences

“…To determine the optimized conditions for the glycosidations to occur, trifluoroacetimidate 16 mannosyl donor 3 was prepared as previously described, 6 and then coupled with a range of monosaccharide acceptors (Scheme 1, Table 1). …”

“…[3][4][5] In this paper we detail the development of an especially rapid approach for achieving partially protected structures 1 and 2 ( Fig. 1), 6 with a particular focus on the optimization of both the glycosidation chemistry and the preparation of the requisite building-blocks.…”

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2009–2010

“…Synthesis of glucuronyl and sulfoglucuronyl oligosaccharides from HNK-1 glycoprotein (Yagi et al, 2008) High-mannose glycans TOF (DHB) Related to HIV gp120. One-pot catalytic glycosidation/Fmoc removal (Pastore et al, 2010b) High-mannose glycans with Glc 3 units TOF (DHB) Study of the conformational properties of the Glc 3 Man unit (Mackeen et al, 2009) High-mannose glycansmethotrexate derivatives TOF Identification of the recognition motif of the glycoprotein-folding sensor enzyme, UDP-Glc: glycoprotein glucosyltransferase…”