A new route for formation of the carbon-phosphorus bond, and synthesis of 1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-5-C-[(R)- and (S)-phenylphosphinyl]-α- and -β-d-xylopyranose

Seo, Kuniaki

doi:10.1016/0008-6215(83)84049-x

Cited by 24 publications

(1 citation statement)

References 15 publications

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“…The preparation of the sensor molecules (R,R)-1 and (S,S)-1 was successful from phosphine oxides (R,R)-8 and (S,S)-8 (Scheme 4). First, ethyl phosphinate (S,S)-6 was reduced to phosphine oxide (S,S)-8 using sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al ® ) in toluene (C) (Scheme 4) [21][22][23]. A higher yield was achieved for this transformation by using lithium aluminum hydride in diethyl ether (D) [24], and because of this the reduction was also carried out by starting from (R,R)-6 (Scheme 4).…”

Section: Results and Discussion 21 Synthesismentioning

confidence: 99%

Synthesis, Fluorescence and NMR Spectroscopic Studies of a Novel Phosphinoxido-18-crown-6 Ether Containing an Anthracene Fluorophore Unit

Szabó-Szentjóbi

Márton

Pál

et al. 2019

Period. Polytech. Chem. Eng.

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The synthesis of the (R,R) and (S,S) enantiomers of a new enantiopure monophospha-18-crown-6 ether (1), which contains an anthracene fluorophore unit and methyl groups at its stereogenic centers, was accomplished. The structure of one enantiomer ((S,S)-1) was studied using one-dimensional (1H, 13C{1H}, and 31P{1H}) and two-dimensional NMR spectra. Because (R,R)-1 and (S,S)-1 can act as new fluorescent chemosensors, we examined their enantiomeric differentiation abilities toward the enantiomers of protonated chiral primary amines and amino acid esters (PEA, 1-NEA, PGME, PAME) using UV-Vis and fluorescence spectroscopies. These monophospha-crown ethers showed moderate enantiomeric discrimination abilities.

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Section: Results and Discussion 21 Synthesismentioning

confidence: 99%

Synthesis, Fluorescence and NMR Spectroscopic Studies of a Novel Phosphinoxido-18-crown-6 Ether Containing an Anthracene Fluorophore Unit

Szabó-Szentjóbi

Márton

Pál

et al. 2019

Period. Polytech. Chem. Eng.

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The Barton‐McCombie Reaction

2012

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Deoxygenations of alcohols, i.e., processes that replace a hydroxyl group with hydrogen at a saturated carbon, find applications in both total synthesis and the systematic modifications of natural products. They may also be employed to introduce deuterium or tritium in a site‐specific manner. Reductive methods that involve ionic or highly polarized reagents or intermediates can be limited in their applicability: for example, competing reaction pathways including cationic rearrangements and anionic eliminations may be encountered in sterically hindered systems with substrates bearing heteroatoms close to the center undergoing reduction. As evidenced by developments over the last few decades, methods that involve the generation and direct quenching via hydrogen atom abstraction of the derived, carbon‐centered radical typically show the greatest tolerance for the presence of other functional groups and for variations in both the steric acid and the electronic environment in the vicinity of the center undergoing deoxygenation. Derivatization of the hydroxyl is a prerequisite, the determinant factors for efficient formation of the deoxygenated product lies in the ability of the combination of the substrate and reagents to induce homolysis of the C‐O bond coupled with the induction of homolysis to rapidly reduce a free radical by hydrogen donation, thereby propagating an efficient chain process. A high‐yielding way to realize this sequence was first described by Barton McCombie using the free‐radical chain reaction of O ‐thioacyl derivatives of secondary alcohols with tri‐ n ‐butylstannane. This chapter provides a detailed description and comparison of the combinations of substrates and reagents that will bring about these processes and provides a summary and evaluation of alternative deoxygenation methods. Mechanistic and stereochemical issues set out the scope and limitations of these processes with respect to both the thioacylation and reduction steps and exemplify some applications to both total synthesis and the modification of natural products.

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ChemInform Abstract: A NEW ROUTE FOR FORMATION OF THE CARBON‐PHOSPHORUS BOND, AND SYNTHESIS OF 1,2,4‐TRI‐O‐ACETYL‐5‐DEOXY‐3‐O‐METHYL‐5‐C‐((R)‐ AND (S)‐PHENYLPHOSPHINYL)‐α‐ AND ‐β‐D‐XYLOPYRANOSE

Seo¹

1984

Chemischer Informationsdienst

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A new route for formation of the carbon-phosphorus bond, and synthesis of 1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-5-C-[(R)- and (S)-phenylphosphinyl]-α- and -β-d-xylopyranose

Cited by 24 publications

References 15 publications

Synthesis, Fluorescence and NMR Spectroscopic Studies of a Novel Phosphinoxido-18-crown-6 Ether Containing an Anthracene Fluorophore Unit

Synthesis, Fluorescence and NMR Spectroscopic Studies of a Novel Phosphinoxido-18-crown-6 Ether Containing an Anthracene Fluorophore Unit

The Barton‐McCombie Reaction

ChemInform Abstract: A NEW ROUTE FOR FORMATION OF THE CARBON‐PHOSPHORUS BOND, AND SYNTHESIS OF 1,2,4‐TRI‐O‐ACETYL‐5‐DEOXY‐3‐O‐METHYL‐5‐C‐((R)‐ AND (S)‐PHENYLPHOSPHINYL)‐α‐ AND ‐β‐D‐XYLOPYRANOSE

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