D-Ribonolactone, A Versatile Synthetic Precursor of Biologically Relevant Scaffolds

Silveira, Gustavo Pozza; Cardozo, Herbert M.; Rossa, Thaís A.; Sá, Marcus M.

doi:10.2174/157017941205150821130147

Cited by 7 publications

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“…11 A complex study involving acetal migration and ring expansion was performed to explain this unexpected result. 5 Thus, the use of D-ribonolactone (2) and its O-acyl derivatives as chiral building blocks relies on the development of a facile method that allows for the correct assignment of the lactone ring-size. 1 13 C NMR spectroscopy was proposed as a method to assign the lactone ring-size, supported by considerable differences in the C-3 and C-4 chemical shifts.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In the case of D-ribose, a five-membered lactone (2) and a six-membered lactone may result (Scheme 2). 5 Although these two lactones can be differentiated using 1 H NMR spectroscopy, 6 the analysis is not straightforward, which is generally true for saccharide-derivative lactones. 1 This laboratory experiment describes the preparation of fiveand six-membered lactones from D-ribose (1) using protocols for 1,2-diol protection.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis and ¹H NMR Spectroscopic Elucidation of Five- and Six-Membered d-Ribonolactone Derivatives

Sales

Silveira

2015

J. Chem. Educ.

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Lactone-size identification of D-ribonolactone derivatives has been debated for four decades due to complex lactone-ring rearrangements and acetal migration. This laboratory experiment for an upper-division undergraduate organic chemistry laboratory course describes a fast and reliable assignment of lactone-size derivatives from D-ribose using 1 H and 1 H− 1 H NOESY NMR spectroscopy. In addition, the further derivatization of these lactones via O-acylation is described, followed by a theoretical study that allows conformational analysis of these molecules in solution using JANOCCHIO software. Overall, this experiment uses simple, inexpensive, and commercially available reagents, and the reactions are performed in mild conditions. The products are solid and can be either purified by crystallization or used directly in the next step of the synthesis. 13 C, 2D 1 H− 1 H COSY, and 1 H− 13 C HMQC or HSQC spectra are also analyzed. Therefore, this laboratory experiment allows students to explore several NMR techniques and relate them with basic NMR concepts, such as scalar coupling constants related to dihedral angles and the NOE effect, to predict lactone-size and conformation of the synthesized molecules in solution.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and ¹H NMR Spectroscopic Elucidation of Five- and Six-Membered d-Ribonolactone Derivatives

Sales

Silveira

2015

J. Chem. Educ.

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“…Subsequent TBDMS deprotection with montmorillonite K10 in a mixture of methanol and water gave d -(+)-ribono-1,4-lactone in 77% yield. d -Ribonolactone has been chosen as a useful intermediate to produce 4-deazaformycin B and (+)-varitriol (antibiotic and antitumoral agents, respectively).…”

Section: Hbo Derivatives As Synthons For Organic Synthesismentioning

confidence: 99%

(S)-γ-Hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity, and Applications

Flourat

Haudrechy

Allais

et al. 2019

Org. Process Res. Dev.

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Chirality is greatly sought for pharmaceutical compounds or fragrance and flavors.(S)-γ-hydroxymethyl-α,β-butenolide, aka HBO, is a chiral (5H)-furanone providing a polarized double bond, a lactone ring and a primary alcohol as playground for synthetic chemists. This molecule has been used for forty years in a wide range of synthetic pathways to natural and/or bioactive molecules. Its own synthesis, always from biosourced product, has also significantly evolved and could be now achieved both at large scale and by applying Green Chemistry principles. This review will explore the syntheses, the reactivity and the uses of HBO.

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“…6 ) has garnered much attention [ 61 – 63 69 – 75 78 ]. Ribonolactone typically with its hydroxy groups protected, is amenable to nucleophilic substitutions [ 78 – 79 ]. Use of C-nucleophiles such as lithiated (hetero)aryls leads to C-C bond via a lactol intermediate ( Fig.…”

Section: Reviewmentioning

confidence: 99%

Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

Temburnikar¹,

Seley‐Radtke²

2018

Beilstein J. Org. Chem.

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C-nucleosides have intrigued biologists and medicinal chemists since their discovery in 1950's. In that regard, C-nucleosides and their synthetic analogues have resulted in promising leads in drug design. Concurrently, advances in chemical syntheses have contributed to structural diversity and drug discovery efforts. Convergent and modular approaches to synthesis have garnered much attention in this regard. Among them nucleophilic substitution at C1' has seen wide applications providing flexibility in synthesis, good yields, the ability to maneuver stereochemistry as well as to incorporate structural modifications. In this review, we describe recent reports on the modular synthesis of C-nucleosides with a focus on D-ribonolactone and sugar modifications that have resulted in potent lead molecules.

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D-Ribonolactone, A Versatile Synthetic Precursor of Biologically Relevant Scaffolds

Cited by 7 publications

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Synthesis and ¹H NMR Spectroscopic Elucidation of Five- and Six-Membered d-Ribonolactone Derivatives

Synthesis and ¹H NMR Spectroscopic Elucidation of Five- and Six-Membered d-Ribonolactone Derivatives

(S)-γ-Hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity, and Applications

Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

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D-Ribonolactone, A Versatile Synthetic Precursor of Biologically Relevant Scaffolds

Cited by 7 publications

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Synthesis and 1H NMR Spectroscopic Elucidation of Five- and Six-Membered d-Ribonolactone Derivatives

Synthesis and 1H NMR Spectroscopic Elucidation of Five- and Six-Membered d-Ribonolactone Derivatives

(S)-γ-Hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity, and Applications

Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

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Synthesis and ¹H NMR Spectroscopic Elucidation of Five- and Six-Membered d-Ribonolactone Derivatives

Synthesis and ¹H NMR Spectroscopic Elucidation of Five- and Six-Membered d-Ribonolactone Derivatives