2-O-Benzylation in D-Gluconamide Derivative Under Basic Conditions with Complete Retention of Stereo-Integrity: Convenient Access to 2-O-benzyl-3,4:5,6- di-O-isopropylidene-D-glucitol and other Differently Protected D-glucitol Derivatives

Manjunath, B. N.; Harikrishna, K.; Aidhen, Indrapal Singh; Varghese, Babu

doi:10.1080/07328300902979503

Cited by 6 publications

(4 citation statements)

References 10 publications

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“…The open chain alkyl/aryl D‐glucosyl ketones 10 were synthesized by addition of Grignard reagent onto the morpholine amide functionality in the gluco ‐configured building block 13 which is readily available in multigram quantities from cheap and commercially available D‐gluconolactone . As a representative example, addition of phenyl magnesium bromide onto the morpholine amide 13 afforded ketone 10 in 70 % yield.…”

Section: Resultsmentioning

confidence: 99%

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Facile Formation of 5‐Acylated‐2‐hydroxymethyl–furans from Open Chain D‐Glucosyl‐Alkyl/ Aryl Ketones

Borkar

Aidhen

2016

ChemistrySelect

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Section: Resultsmentioning

confidence: 99%

“…To further enhance the utility of this new route for 5‐acylated‐2‐hydroxymethyl‐furans, it was contested to use α‐hydroxyl amide 15 itself and not the α‐ O ‐benzyl protected amide 13 , as it would circumvent an additional protection step.…”

Section: Resultsmentioning

confidence: 99%

Facile Formation of 5‐Acylated‐2‐hydroxymethyl–furans from Open Chain D‐Glucosyl‐Alkyl/ Aryl Ketones

Borkar

Aidhen

2016

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“…This understanding gained a firm footing, when we observed facile conversion of aryl ketones 72 to 5‐acyl‐2‐hydroxymethyl‐furans 73 under acidic conditions (Scheme 12). [56] The aryl‐ketones 72 were conveniently made through direct nucleophilic addition of Grignard agents on to the morpholine amide 71 [57] . Since L‐tartaric acid, meso ‐erythritol and D‐gluconolactone, are all part of nature's biomass abundance, these conversions are likely to gain significance under the broad realm of defunctionalization of carbohydrates for value added chemicals [58]…”

Section: Research Work At Iit‐madrasmentioning

confidence: 99%

“…[56] The arylketones 72 were conveniently made through direct nucleophilic addition of Grignard agents on to the morpholine amide 71. [57] Since L-tartaric acid, meso-erythritol and D-gluconolactone, are all part of nature's biomass abundance, these conversions are likely to gain significance under the broad realm of defunctionalization of carbohydrates for value added chemicals. [58] The convenience of acyl-anion chemistry inspired us to explore the possible synthesis of unknown C-aryl septanosides 74 through the disconnection presented in figure 7.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Natural Products & Bioactivity Inspired Synthetic Pursuits Interfacing with Carbohydrates: Ongoing Journey with C‐Glycosides

Aidhen

Thoti

2021

The Chemical Record

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Natural products, remains the most important source for the discovery of new drugs for the treatment of human diseases. This has inspired the synthetic community to design and develop mimics of natural products either to answer important questions in biology or to explore their therapeutic potentials. Glycosides present themselves abundantly in nature, right from the cell surface receptors to natural products of any origin. The O-Glycosides are hydrolytically less stable compared to C-glycosides and this feature has presented a great opportunity for drug discovery. The discovery of Dapagliflozin, an SGLT inhibitor and C-glucoside, for the treatment of diabetes is one such example. Aryl acyl-anion chemistry has been explored for the synthesis of 2-deoxy-C-aryl furanoside/pyranoside/septanosides. Besides success, the studies have provided valuable insight into the natural propensities of the architectural framework for the cascade to furan derivatives. The aryl acyl-anion chemistry has also enabled the synthesis of biologically active diaryl heptanoids. Inspired from sucesss of Dapagliflozin, new analogues have been synthesized with pyridine and isocoumarin heterocycle as the proximal ring. C-glucosides of isoliquiritigenin have been synthesized for the first time and evaluated as an efficient aldose reductase inhibitor. The synthesis and evaluation of acyl-C-β-D-glucosides and benzyl-C-β-Dglucoside as glucose-uptake promoters has revealed promise in small molecules. The concept of building blocks has been used to obtain natural oxylipins, D-xylo and L-xylo-configured alkane tetrols and novel lipophilic ketones with erythro/threo configured trihydroxy polar head-group as possible anti-mycobacterial agents.

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ChemInform Abstract: 2‐O‐Benzylation in D‐Gluconamide Derivative under Basic Conditions with Complete Retention of Stereo‐Integrity: Convenient Access to 2‐O‐Benzyl‐3,4:5,6‐di‐O‐isopropylidene‐D‐glucitol and Other Differently Protected D‐Glucitol Derivatives.

Manjunath¹,

Harikrishna²,

Aidhen³

et al. 2009

ChemInform

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tives. -The search for an alternative procedure for the synthesis of chiral building block (VIIg) results in an efficient general synthesis of compounds of type (VII) on multigram scale. This approach starts with gluconate (II), conveniently available in a single step from D-gluconolactone (I). Reacting (II) with morpholine (III) affords the hitherto unknown α-hydroxy morpholine amide (IV) as a solid. The convenience in using NaBH4 for the reduction of (VI) offers a significant advantage to this alternative procedure for (VIIg).

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2-O-Benzylation in D-Gluconamide Derivative Under Basic Conditions with Complete Retention of Stereo-Integrity: Convenient Access to 2-O-benzyl-3,4:5,6- di-O-isopropylidene-D-glucitol and other Differently Protected D-glucitol Derivatives

Cited by 6 publications

References 10 publications

Facile Formation of 5‐Acylated‐2‐hydroxymethyl–furans from Open Chain D‐Glucosyl‐Alkyl/ Aryl Ketones

Facile Formation of 5‐Acylated‐2‐hydroxymethyl–furans from Open Chain D‐Glucosyl‐Alkyl/ Aryl Ketones

Natural Products & Bioactivity Inspired Synthetic Pursuits Interfacing with Carbohydrates: Ongoing Journey with C‐Glycosides

ChemInform Abstract: 2‐O‐Benzylation in D‐Gluconamide Derivative under Basic Conditions with Complete Retention of Stereo‐Integrity: Convenient Access to 2‐O‐Benzyl‐3,4:5,6‐di‐O‐isopropylidene‐D‐glucitol and Other Differently Protected D‐Glucitol Derivatives.

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