Regioselective, One‐Pot Functionalization of Carbohydrates

Kulkarni, Suvarn S.

doi:10.1002/9783527696239.ch12

Cited by 2 publications

(1 citation statement)

References 82 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Benzylidene acetals are key intermediates in tandem functionalization reactions that deliver orthogonally protected carbohydrate derivatives from per- O -silylated intermediates. , Silyl triflates, copper(II) triflate, and iron(III) chloride hexahydrate have been employed in these types of protocols, which enable substitutions of trimethylsilyl (TMS) groups for acetals, esters, or other silyl groups, as well as reductive ring-opening reactions of acetals, to be conducted in a single reaction flask. Scheme depicts the preparation of an orthogonally protected α-glucopyranoside derivative by sequential 4,6- O -benzylidene formation, reductive etherification, and acetylation …”

Section: Formation Of Cyclic Adducts From 12- or 13-diol Moieties: Ac...mentioning

confidence: 99%

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

2018

View full text Add to dashboard Cite

Methods for site-selective transformations of hydroxyl groups in carbohydrate derivatives are reviewed. The construction of oligosaccharides of defined connectivity hinges on such transformations, which are also needed for the preparation of modified or non-natural sugar derivatives, the installation of naturally occurring postglycosylation modifications, the selective labeling or conjugation of carbohydrate derivatives, and the preparation of therapeutic agents or research tools for glycobiology. The review begins with a discussion of intrinsic factors and processes that can influence selectivity in reactions of unprotected or partially protected carbohydrate derivatives, followed by a description of transformations that engage two OH groups in cyclic adducts (acetals, ketals, boronic esters, and related species). An overview of the various classes of site-selective transformations of OH groups in sugars is then provided: the reactions discussed include esterification, thiocarbonylation, alkylation, glycosylation, arylation, silylation, phosphorylation, sulfonylation, sulfation, and oxidation. Emphasis is placed on recently developed methods that employ reagent or catalyst control to achieve otherwise challenging transformations or site-selectivities.

show abstract

Section: Formation Of Cyclic Adducts From 12- or 13-diol Moieties: Ac...mentioning

confidence: 99%

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

2018

View full text Add to dashboard Cite

show abstract

Advances in Protecting Groups for Oligosaccharide Synthesis

Ghosh

Kulkarni

2020

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

Carbohydrates contain numerous hydroxyl groups and sometimes amine functionalities which lead to a variety of complex structures. In order to discriminate each hydroxyl group for the synthesis of complex oligosaccharides, protecting group manipulations are essential. Although the primary role of a protecting group is to temporarily mask a particular hydroxyl/amino group, it plays a greater role in tuning the reactivity of coupling partners as well as regioselectivity and stereoselectivity of glycosylations. Several protecting groups offer anchimeric assistance in glycosylation. They also alter the solubility of substrates and thereby influence the reaction outcome. Since oligosaccharides comprise branched structures, the glycosyl donors and acceptors need to be protected with orthogonal protected groups that can be selectively removed one at a time without affecting other groups. This minireview is therefore intended to provide a discussion on new protecting groups for amino and hydroxyl groups, which have been introduced over last ten years in the field of carbohydrate synthesis. These protecting groups are also useful for synthesizing non‐carbohydrate target molecules as well.

show abstract

Regioselective, One‐Pot Functionalization of Carbohydrates

Cited by 2 publications

References 82 publications

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

Advances in Protecting Groups for Oligosaccharide Synthesis

Contact Info

Product

Resources

About