Synthesis of a trigalacturonic acid analogue mimicking the expected transition state in the glycosidases

Solvent-Free One-Pot Diversified Protection of Saccharide Polyols Via Regioselective Tritylations

“…Only in the case of the di‐ O ‐tritylation of allyl lactoside 7 (entry 8), an additional amount of pyridine was added in the course of the reaction, with a beneficial effect on both mobility of the mixture and reaction yield. Collectively, results in Table indicate that with a range of substrates, solvent‐free tritylations performed at 70–100 °C are much faster than under standard solution conditions; indeed from a survey of the literature, a very few number of examples were found of saccharide O ‐tritylations lasting less than 4 hours,,, also including procedures relying, unlike the protocols herein described, on DMAP catalysis.…”

Profiling Glycosylphosphatidylinositol (GPI)-Interacting Proteins in the Cell Membrane Using a Bifunctional GPI Analogue as the Probe

“…23 The synthesis of probe 2, as outlined in Scheme 1, commenced with the conversion of commercially available methyl αglucopyranoside 3 into 6 by a literature procedure. 36 Regioselective 4,6-O-benzylidenation of 3 upon reaction with benzaldehyde dimethyl acetal and camphorsulfonic acid (CSA) followed by protecting the remaining free hydroxyl groups in 4 with the para-methoxybenzyl (PMB) group afforded 5 in a 71% yield for two steps. PMB ethers can be selectively cleaved under mildly acidic conditions later.…”

H2SO4-Silica: An Efficient Promoter for Selective Removal of Benzylidene and Isopropylidene Groups in the Presence ofp-Methoxybenzyl Group

“…[9] However, removal of benzylidene and isopropylidene protections in the presence of the p-methoxybenzyl group is rare in the literature. [10,11] This is primarily due to the acid-labile nature of the p-methoxybenzyl group that results in removal of the group along with the benzylidene and isopropylidene protections. With our experience using H 2 SO 4 -silica [12][13][14][15][16][17][18][19][20][21] as a mild acid source for various carbohydrate transformations, we envisaged that it might provide the adequate acidity for the hydrolysis of the benzylidene and isopropylidene protections without affecting the p-methoxyphenyl group.…”