Recent chemical syntheses of bacteria related oligosaccharides using modern expeditious approaches.

Apart from some essential and crucial roles in life processes carbohydrates also are involved in a few detrimental courses of action related to human health, like infections by pathogenic microbes, cancer metastasis, transplanted tissue rejection, etc. Regarding management of pathogenesis by microbes, keeping in mind of multi drug-resistant bacteria and epidemic or endemic incidents, preventive measure by vaccination is the best pathway as also recommended by the WHO; by vaccination, eradication of bacterial diseases is also possible. Although some valid vaccines based on attenuated bacterial cells or isolated pure polysaccharide-antigens or the corresponding conjugates thereof are available in the market for prevention of several bacterial diseases, but these are not devoid of some disadvantages also. In order to develop improved conjugate T-cell dependent vaccines oligosaccharides related to bacterial antigens are synthesized and converted to the corresponding carrier protein conjugates. Marketed Cuban Quimi-Hib is such a vaccine being used since 2004 to resist Haemophilus influenza b infections. During nearly the past two decades research is going on worldwide for improved synthesis of bacteria related oligosaccharides or polysaccharides towards development of such semisynthetic or synthetic glycoconjugate vaccines. The present dissertation is an endeavour to encompass the recent syntheses of several pathogenic bacterial oligosaccharides or polysaccharides, made during the past ten-eleven years with special reference to modern expeditious syntheses.

A metal free mild and green approach for tandem opening of 4,6-O-benzylidene acetals to their corresponding 6-O-acetyl derivatives: Application in the synthesis of a trisaccharide using one-pot glycosylation reactions.

An efficient and high yielding reaction for tandem opening of 4,6-O-benzylidene derivatives (gluco, galacto, manno, 2-phthalimido-2-deoxy glucosides) to their corresponding 6-O-acetyl derivatives has been established under metal free condition using 60% solution of aqueous acetic acid (v/v). The reaction is equally pertinent for large scale synthesis and also for disaccharide glycosides. Its application for the construction of a building block towards synthesis of a trisaccharide part related to Pseudomonas aeruginosa utilizing one-pot glycosylation reactions has also been described.

Carbohydrate Derived Organogelators and the Corresponding Functional Gels Developed in Recent Time.

Owing to their multifarious applicability, studies of molecular and supramolecular gelators and their corresponding gels have gained momentum, particularly in the last two decades. Hydrophobic⁻hydrophilic balance, different solvent parameters, gelator⁻gelator and gelator⁻solvent interactions, including different noncovalent intermolecular interactive forces like H-bonding, ionic interactions, π⁻π interactions, van der Waals interactions, etc., cause the supramolecular gel assembly of micro and nano scales with different types of morphologies, depending on the gelator, solvent, and condition of gelation. These gel structures can be utilized for making template inorganic superstructures for potential application in separation, generation of nanocomposite materials, and other applications like self-healing, controlled drug encapsulation, release and delivery, as structuring agents, oil-spill recovery, for preparation of semi-conducting fabrics, and in many other fields. Sugars, being easily available, inexpensive, and nontoxic natural resources with multi functionality and well-defined chirality are attractive starting materials for the preparation of sugar-based gelators. This review will focus on compilation of sugar derived organogelators and the corresponding gels, along with the potential applications that have been developed and published recently between January 2015 and March 2018.

Trichloroisocyanuric acid (TCCA): an efficient green reagent for activation of thioglycosides toward hydrolysis.

Trichloroisocyanuric acid (TCCA), an inexpensive, commercially available, and non-toxic reagent has been used for the activation of thioglycosides toward their hydrolysis to the corresponding hemiacetals in high to excellent yields. The methodology provides a mild reaction condition for dealing with compounds containing acid sensitive functional groups.

Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf.

N-(p-Methylphenylthio)-ε-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy.

FeCl3 mediated arylidenation of carbohydrates.

Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl(3)-catalyzed (20 mol%) regioselective 4,6-O-arylidenation producing the corresponding acetals in high yields. FeCl(3) also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4',6'-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn.