The use of levoglucosenone and isolevoglucosenone as templates for the construction of C-linked disaccharides

Awad, Loay; Demange, Raynald; Zhu, Yugen; Vogel, Pierre

doi:10.1016/j.carres.2006.04.008

Cited by 33 publications

(6 citation statements)

References 217 publications

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“…[15] Other uses of LGO can be found elsewhere. [8,16] The chemical synthesis of LGO and its enantiomer from various precursors has been described. [17] The traditional method of cellulose pyrolysis for preparation of LGO is still a viable and economically feasible procedure.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Fast Pyrolysis of Cellulose to Prepare Levoglucosenone Using Sulfated Zirconia

et al. 2010

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Sulfated zirconia was employed as catalyst for fast pyrolysis of cellulose to prepare levoglucosenone (LGO), a very important anhydrosugar for organic synthesis. The yield and the selectivity of LGO were studied in a fixed-bed reactor at different temperatures and cellulose/catalyst mass ratios. The experiments of catalyst recycling were also carried out. The results displayed that from 290 to 400 °C, the liquid and solid accounted for more than 95 wt % of products, and the higher temperature led to more liquid and less solid products. The introduction of SO₄²⁻/ZrO₂ could promote cellulose conversion and LGO production. The temperature had a similar effect on the yield and selectivity of LGO at different cellulose/catalyst mass ratios. The maximum yield was obtained at 335 °C. Although the structure of the parent ZrO₂ was retained after recycles, which was confirmed by X-ray diffraction and N₂ adsorption-desorption measurements, the activity of SO₄²⁻/ZrO₂ could only be partially recovered by simply calcination. The catalytic activity decrease could be mainly attributed to SO₄²⁻ leaching, and the activity could be restored by further impregnation of H₂SO₄.

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Section: Introductionmentioning

confidence: 99%

Catalytic Fast Pyrolysis of Cellulose to Prepare Levoglucosenone Using Sulfated Zirconia

et al. 2010

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“…Heck reactions with LGO as the alkene seemed another exciting and unexplored way to derivatize the 2‐position of LGO. We envisaged that hydrogenation of product 5 would occur from the face opposite the anhydro bridge to give derivatives epimeric to those obtained from conjugate addition reactions with organometallic reagents 18. A compounding factor in these reactions is that the palladium‐catalyzed hydroarylation reaction14 (formal conjugate addition) competes with the Heck reaction of LGO.…”

Section: Resultsmentioning

confidence: 99%

Palladium‐Catalyzed Suzuki–Miyaura, Heck and Hydroarylation Reactions on (–)‐Levoglucosenone and Application to the Synthesis of Chiral γ‐Butyrolactones

et al. 2015

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The chiral pool material (–)‐levoglucosenone (6,8‐dioxabicyclo[3.2.1]oct‐2‐en‐4‐one, LGO) has been substituted by using a series of Pd‐mediated cross‐coupling reactions. Iodination of LGO followed by Suzuki–Miyaura cross‐coupling reaction with boronic acids by employing the Buchwald ligand SPhos with Pd(OAc)2 afforded 3‐aryl derivatives in excellent yields. Selective Heck arylation reaction at the 2‐position was achieved with aryl iodides with K3PO4 as base and SPhos ligand with Pd(OAc)2 (1–5 mol‐%). A selective hydroarylation reaction (formal conjugate addition) was developed by using the same aryl iodides, benzyldiethylamine, Pd(OAc)2, and P(o‐tol)3. The products were converted, either directly or after alkene reduction, through a Baeyer–Villiger oxidation into chiral 3‐ and 4‐substituted 5‐(hydroxymethyl)dihydrofuran‐2(3H)‐ones.

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“…Indeed, this aldehyde is a sensitive material that degrades easily under basic conditions or upon contact with silica gel. Fortunately, the Michael step afforded product of excellent quality, enabling the conduct of a subsequent Baylis−Hillman reaction without purification. The kinetics of the latter process are notoriously slow, and in fact formation of 64 required 2 days even by operating in neat acrylonitrile.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Studies toward Sordarin: Building Blocks for the Terpenoid Core and for Analogues Thereof

et al. 2009

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The use of levoglucosenone and isolevoglucosenone as templates for the construction of C-linked disaccharides

Cited by 33 publications

References 217 publications

Catalytic Fast Pyrolysis of Cellulose to Prepare Levoglucosenone Using Sulfated Zirconia

Catalytic Fast Pyrolysis of Cellulose to Prepare Levoglucosenone Using Sulfated Zirconia

Palladium‐Catalyzed Suzuki–Miyaura, Heck and Hydroarylation Reactions on (–)‐Levoglucosenone and Application to the Synthesis of Chiral γ‐Butyrolactones

Synthetic Studies toward Sordarin: Building Blocks for the Terpenoid Core and for Analogues Thereof

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