Article
Chemistry, Multidisciplinary
Yu Yang, Nan Jiang, Yuling Mei, Zekun Ding, Jianbo Zhang
Summary: A sustainable magnetic core-shell nanocatalyst Fe3O4@C@Fe(III) was successfully used for the synthesis of a series of 2-nitro-2,3-unsaturated O-glycosides with high yields and stereoselectivity. The catalyst exhibited wide substrate applicability, including different kinds of alcohols and structurally complex acceptors. In addition, the catalyst could be easily separated and reused multiple times without significant decrease in catalytic performance.
FRONTIERS IN CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Yogesh Yadav, Rajdeep Tyagi, Kanchan Yadav, Ghanshyam Tiwari, Ram Sagar
Summary: The Ferrier rearrangement using SnCl4 as catalyst allows for the synthesis of 2,3-unsaturated glycopyranosides with high stereoselectivity starting from the hydroxyl group at the C-3 position. This method has several advantages, including strong anomeric selectivity, high yields, and short reaction time.
CARBOHYDRATE RESEARCH
(2023)
Article
Biochemistry & Molecular Biology
Kavita Singh, Sourav Sagar Behera, Rajdeep Tyagi, Ghanshyam Tiwari, Ram Sagar
Summary: A metal free synthesis of enantiopure 2,3-dideoxy-α, β-unsaturated carbohydrate enals (Perlin aldehydes) in CH3CN-0.02 N H2SO4 in water (1:1, v/v) with additives has been reported. The protocol works well for acetylated glycals, providing Perlin aldehydes and hemiacetals in good yields. The use of 0.02 N H2SO4 in water: acetonitrile (1:1, v/v) solvent system is essential for Perlin aldehyde formation.
CARBOHYDRATE RESEARCH
(2023)
Review
Chemistry, Physical
Giulio Goti
Summary: This article discusses the application of catalytic radical methods in the functionalization of unsaturated carbohydrates, highlighting the opportunities they offer for new reaction design. These methods overcome the limitations of classical protocols and provide new routes for the synthesis of complex carbohydrates.
Article
Chemistry, Organic
Agustin H. Rojas, Leticia Lafuente, Virginia Vetere, Agustin Ponzinibbio
Summary: This study presents the selective synthesis of new 2-iodo-2,3-unsaturated O- and S-glycosides, marking the first report on the Ferrier rearrangement of 2-halo-glycals with S-nucleophiles. The alpha-glycosides were obtained in good yields and with high anomeric selectivity. Additionally, the particular behavior of heteroaromatic thio sugar derivatives, including an alternative mechanism for C3 addition, was described, with a complete structure and conformation analysis provided by NMR.
TETRAHEDRON LETTERS
(2021)
Article
Polymer Science
Ryo Miyazaki, Misaki Suzuki, Sangeetha Srinivasa Shetty, Taichi Shimazaki, Issey Osaka, Noriyuki Nakajima, Masahiro Hamada, Yasuhito Koyama
Summary: We investigated the polymerization behavior of galactose-based cyclic sulfite as a monomer used to develop (1 -> 2)-galactan graft polymerization. Galactose-based cyclic sulfite 6 was prepared from tri-O-acetyl-D-galactal and underwent ring-opening polycondensation to give benzylated (1 -> 2)-galactan with the elimination of SO2 under catalytic conditions. The obtained polymer showed a simple mass spectrum pattern suggesting the formation of benzylated (1 -> 2)-galactan with OH groups at both ends.
Article
Polymer Science
Ryo Miyazaki, Misaki Suzuki, Sangeetha Srinivasa Shetty, Taichi Shimazaki, Issey Osaka, Noriyuki Nakajima, Masahiro Hamada, Yasuhito Koyama
Summary: The polymerization behavior of galactose-based cyclic sulfite as a monomer for the graft polymerization preparation of (1 -> 2)-galactan was investigated. Different initiators were used to study the polymerization reaction, and the mechanism was probed systematically.
Article
Chemistry, Organic
Debora Pratesi, Stefania Mirabella, Giulia Petrucci, Camilla Matassini, Cristina Faggi, Francesca Cardona, Andrea Goti
Summary: Glycosylamine derivatives, which are biologically relevant compounds, can be synthesized by utilizing the allyl cyanate to isocyanate rearrangement of carbamate-substituted glycals, followed by nucleophilic addition with alcohols or amines. The reaction proceeds through a [3,3]-sigmatropic pericyclic mechanism and exhibits stereospecificity. The synthesized unsaturated N-glycosides can be selectively cis-dihydroxylated to obtain different 1-aminosugars.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Narayanaswamy Jayaraman
Summary: Unsaturated monosaccharides expand the reactivity scope in sugars, leading to new methodologies, molecular structures, and functional entities. Endocyclic or exocyclic unsaturation as reactive moieties can lead to largely unknown structures through one carbon homologations. Molecular shifts and rearrangements allow interchanging reactivities from one carbon to another in unsaturated sugars, with activations of exocyclic unsaturated sugars offering newer possibilities to sugar chemistry reactions. Personal reflections stem from decades of explorations in unsaturated sugars from varied perspectives.
Review
Chemistry, Multidisciplinary
Nazar Hussain, Faheem Rasool, Shahnawaz Khan, Mohd Saleem, Mittali Maheshwari
Summary: Glycals are versatile building blocks for the synthesis of C-glycosides, branched sugars, and natural products. They are easily available and possess inherent chirality, making them useful for the chiral synthesis of natural products and pharmaceuticals.
Article
Chemistry, Organic
Ramu Sridhar Perali, Umamaheswara Rao Boddu, Drisya Chittadi Sankar
Summary: The study presents a simple and efficient strategy for the regio- and stereoselective synthesis of carbon-branched sugar derivatives. By implementing Wittig rearrangement on substrates derived from various glycals and 3-O-alkenyl glycals through Ferrier rearrangement, a highly selective [1,2]- or [2,3]-Wittig rearrangement is revealed, providing a novel class of stereodefined 3-C-branched glycals and C-glycosides that are otherwise difficult to obtain.
Article
Multidisciplinary Sciences
Li Li, Kun Deng, Yajie Xing, Cheng Ma, Shao-Fei Ni, Zhaofeng Wang, Yong Huang
Summary: This article reports the synthesis of a class of hypervalent iodine reagents with a transferrable sulfoxonium group, which can react with unsaturated bonds such as alkenes, alkynes, nitriles, and allenes to form sulfoxonium-containing cyclic structures.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Xiang Wang, Wei Ping, Abdol Ghaffar Ebadi, Soma Majedi, Zinatossadat Hossaini, Mohsen Toughani
Summary: This review summarizes recent progress and mechanistic discussions in the synthesis of hydroxymethylalcohols through direct hydroxymethylation of unsaturated hydrocarbons using CO2 as the carbonyl source. The paper is divided into three sections focusing on alkenes, allenes, and alkynes, respectively.
JOURNAL OF CO2 UTILIZATION
(2021)
Article
Chemistry, Applied
Atul Dubey, Neha Singh Chauhan, Zanjila Azeem, Pintu Kumar Mandal
Summary: A Pd(II)-catalyzed, bidentate directing group (BDG)-assisted C(sp(2))-H functionalization of C2-amido glycals onto the anomeric position is reported as a contemporary approach for the synthesis of various unsymmetrical gem-diarylmethyl C-glycosides. The use of a bidentate amidoquinoline-type directing group enables the insertion of different para-quinone methides (p-QMs) onto the pseudo-anomeric position of glycal substrates, yielding moderate to good yields. The final product can be further functionalized through known palladium-catalyzed cross-coupling reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Construction & Building Technology
Dingshi Chen, Kangkang Yang, Dalin Hu, Jun Shi
Summary: This paper establishes a prediction model of chloride transport in unsaturated concrete based on the transport model of moisture. Experimental and simulation studies validate the rationality of the model and show that the random distribution of aggregates significantly influences chloride transport.
CONSTRUCTION AND BUILDING MATERIALS
(2021)
Article
Chemistry, Organic
Thurpu Raghavender Reddy, Dodla Sivanageswara Rao, Kalvacherla Babachary, Sudhir Kashyap
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Govindareddy Kundoor, Dodla Sivanageswara Rao, Sudhir Kashyap
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Dodla S. Rao, Thurpu R. Reddy, Kalvacherla Babachary, Sudhir Kashyap
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Suresh Kumar Battina, Sudhir Kashyap
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Organic
Dodla S. Rao, Thurpu R. Reddy, Sudhir Kashyap
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Organic
Dodla S. Rao, Thurpu R. Reddy, Aakanksha Gurawa, Manoj Kumar, Sudhir Kashyap
Article
Chemistry, Organic
Manoj Kumar, Aakanksha Gurawa, Nitin Kumar, Sudhir Kashyap
Summary: A direct and highly stereoselective glycosylation reaction catalyzed by Bi(OTf)(3) has been reported. The chemoselectivity of deactivated glycal donors can be controlled by tuning the solvent, leading to improved substrate scope. The versatility of this method has been demonstrated in the synthesis of oligosaccharides, as well as the 2-deoxyglycosylation of high-value natural products and drugs.
Article
Chemistry, Multidisciplinary
Aakanksha Gurawa, Manoj Kumar, Sudhir Kashyap
Summary: The study reports a new photolytic radical-induced vicinal azidooxygenation reaction method, which can efficiently convert various functionalized substrates, including unactivated alkenes, and form high-value drug analogs and bioactive skeletons in late-stage transformations.
Article
Chemistry, Multidisciplinary
Manoj Kumar, Nitin Kumar, Aakanksha Gurawa, Sudhir Kashyap
Summary: An alternative and highly efficient method for L-rhamnosylation using ruthenium reagent as a dual catalyst has been developed. This method allows the synthesis of biologically active α-L-rhamnopyranosides in good yields and can tolerate diverse functional groups.
Article
Biochemistry & Molecular Biology
Manoj Kumar, Nitin Kumar, Aakanksha Gurawa, Sudhir Kashyap
Summary: We report a convenient and highly stereocontrolled approach for the synthesis of rare and vital D-talo and D-gulo sugars directly from economical D-galactal. This method, involving dual ruthenium-catalysis, achieves stereo-divergent synthesis through judicious selection of stereoelectronically diverse protecting groups. The synthetic utility of this approach has been demonstrated for the efficient assembly of D-talose and D-gulose sugars in natural products and bioactive scaffolds.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Organic
Aakanksha Gurawa, Nitin Kumar, Sudhir Kashyap
Summary: This article presents a photo-induced method for the synthesis of vinyl sulfones and sulfonates, using sulfonium iodate species. The reaction shows high regioselectivity and substrate tolerance, making it an efficient and atom-economical synthetic approach.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Aakanksha Gurawa, Manoj Kumar, Sudhir Kashyap
Summary: The developed protocol allows for selective deprotection of acetyl groups in a wide range of substrates, including carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The environmentally friendly reagent system used in this method enables clean transformations under ambient conditions.
Article
Chemistry, Multidisciplinary
Aakanksha Gurawa, Manoj Kumar, Dodla S. Rao, Sudhir Kashyap
NEW JOURNAL OF CHEMISTRY
(2020)
Article
Chemistry, Organic
Manoj Kumar, Thurpu Raghavender Reddy, Aakanksha Gurawa, Sudhir Kashyap
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Thurpu Raghavender Reddy, Dodla Sivanageswara Rao, Sudhir Kashyap
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
