Preparation of glycosyl thiourea derivatives from glycosyl azides using sulfamic acid and sodium iodide in one-pot

Gucchait, Arin; Jana, M. K.; Jana, Kuladip; Misra, Anup Kumar

doi:10.1016/j.carres.2016.09.002

Cited by 6 publications

(4 citation statements)

References 28 publications

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“…However, drawbacks including the instability of the glycosyl isothiocyanates or glycosyl amines impose serious limitations of the proposed methods. Therefore, a method based on the one‐pot direct reaction of glycosyl azides with aryl isothiocyanates in the presence of SA and sodium iodide was adopted for the synthesis glycosyl thiourea derivatives [151] (Scheme 83). The study demonstrated the achievement of a number of derivatives in good yields of 58–76 %.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Chopra

Lambat²,

Mahmood

et al. 2021

ChemistrySelect

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In recent times, synthetic organic reactions have gained significant attention as they are becoming a versatile tool in the synthesis of pharmaceuticals, agrochemicals and their intermediates. Sulfamic acid (SA) is an acid catalyst that demonstrated high efficiency in various organic transformations that will be highlighted in this review. These include efforts to develop green approaches using SA catalyst for the CÀ C bond formation reactions and functional group trans-formations, as well as the synthesis of various OÀ and Nheterocyclic compounds and other miscellaneous reactions including multicomponent reactions. The easy recovery (for subsequent reuse) of the catalyst by filtration without the need for solvents is an important advantage of SA catalyst. In this review, SA promoted greener methodologies that were developed and the applicability of these methodologies are addressed.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Chopra

Lambat²,

Mahmood

et al. 2021

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…To prevent difficulty associated with preparation of glycosylamines, a one pot protocol for glycosyl thiourea derivatives from glycosyl azides using sulfamic acid and sodium iodide was explored by Misra group (Scheme 39). [57] The glycosyl azide firstly in situ reduced to glycosylamine that immediately reacts with aryl isothiocyanate to produce glycosyl thiourea derivatives in the presence of sulfamic acid and sodium iodide with excellent yield. Library of glyco-hydantoin conjugates was explored by Volonterio group [58] via one-pot multicomponent sequential process using glyco-azides, isocyanates, and suitable carboxylic acids.…”

Section: Eurjocmentioning

confidence: 99%

An Overview on the ChemicalN‐Functionalization of Sugars and Formation ofN‐Glycosides

2020

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Its even more than a centennial that the systematic researches of chemical alteration of sugars have been advancing. Out of all the interest in the field of N‐glycoside has assembled pace over the past few years. Therefore, N‐functionalization of sugar is one of the most fundamental modifications along with other group like azide, amide etc also play a remarkable role in the field of glycoscience. Different approaches to access structurally modified N‐glycosides in carbohydrate derivatives are reviewed. The goal of this review is to provide an overview of different way of N‐functionalization of amino sugar and induction of nitrogen scaffolds for the synthesis of various orthogonal protective groups of the N‐glycoside. The N‐functionalization of sugars designate as follows: (a) glycosylamine, (b) glycosyl azide, and (c) introduction of N‐functionality to the sugar for formation of N‐glycosides. This is the first review focus on N‐functionalization of sugars which will be a future scope that influence the readers to work in this area further.

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“…It has desirable water descaling properties, low volatility, and low toxicity compared to most common strong mineral acids. 23 Moreover, when sulfamic acid is used as a modifier to treat starch, the number of strongly hydrophilic sulfonic acid groups can be increased to obtain acid-modified starch. It is hypothesized that using acid-modified starch might improve the hydrophilicity and salt tolerance of starch-based SAPs.…”

Section: Introductionmentioning

confidence: 99%

“…Sulfamic acid is a moderately strong acid and might be considered to be an intermediate compound between sulfuric acid and sulfamide. It has desirable water descaling properties, low volatility, and low toxicity compared to most common strong mineral acids . Moreover, when sulfamic acid is used as a modifier to treat starch, the number of strongly hydrophilic sulfonic acid groups can be increased to obtain acid-modified starch.…”

Section: Introductionmentioning

confidence: 99%

Salt-Tolerant Superabsorbent Polymer with High Capacity of Water-Nutrient Retention Derived from Sulfamic Acid-Modified Starch

et al. 2019

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The application of superabsorbent polymers (SAPs) is hindered because their absorption capability is greatly affected by the electrolytes in a solution. A novel modified water-absorbent polymer was fabricated by solution polymerization of sulfamic acid-modified starch and acrylic acid; the swelling ratios of this absorbent polymer were 1026 g/g in deionized water and 145 g/g in 0.9% sodium chloride solution and increased by 99.5 and 13.4%, respectively, when compared with ordinary starch-grafted acrylic SAPs. The water absorption capacity was measured in water at different pH values, salt concentrations, and temperatures. In addition, water and fertilizer retentions were studied by simulated leaching tests in a soil column. The results showed that water absorption capacities of the modified SAP in salt solutions were improved due to the adsorption and transfer of water molecules by the sulfonic acid groups. Compared to the losses when there was no superabsorbent treatment, the water, nitrate, ammonium nitrogen, and water-soluble potassium losses during the salt-tolerant superabsorbent treatment were significantly reduced by 18.5, 22.8, 88.0, and 63.8%, respectively. The method introduced in this study could guide the development and wide application of salt-tolerant SAPs in agriculture and horticulture.

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Preparation of glycosyl thiourea derivatives from glycosyl azides using sulfamic acid and sodium iodide in one-pot

Cited by 6 publications

References 28 publications

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

Sulfamic Acid as Versatile Green Catalyst Used For Synthetic Organic Chemistry: A Comprehensive Update

An Overview on the ChemicalN‐Functionalization of Sugars and Formation ofN‐Glycosides

Salt-Tolerant Superabsorbent Polymer with High Capacity of Water-Nutrient Retention Derived from Sulfamic Acid-Modified Starch

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