Further examples of orthoesterification under kinetically controlled conditions application to the selective acylation of sucrose, maltose and α,α-trehalose

Bouchra, M.; Gelas, Jacques

doi:10.1016/s0008-6215(97)00208-5

Cited by 7 publications

(2 citation statements)

References 11 publications

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“…The 1 H NMR spectra for anhydrous a,a-trehalose, carried out in dry DMSO-d 6 solution at ambient temperature, is in agreement with the one reported by Bouchra and Gelas in Me 2 CO(d 6 ) [11].…”

Section: Sample Characterizationsupporting

confidence: 88%

“…It is known that trehalose is suitable for drug protection (the high temperature of the glass transition is crucial to increasing drug stability and shelf life) [3], for storage of living cells and tissues for many potential clinical applications (avoiding cryogenic solutions) [9][10][11][12][13], and for a variety of applications in processed food (beverages, frozen foods, and chocolate confectionery) [14,15]. Several studies of trehalose in condensed phase [16][17][18][19][20][21][22][23], aqueous phase [24], and computational chemistry [25,26] related with anhydrous trehalose and trehalose dihydrate were carried out.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Crystalline anhydrous α,α-trehalose (polymorph β) and crystalline dihydrate α,α-trehalose: A calorimetric study

Pinto¹,

Diogo²,

Ramos³

2006

The Journal of Chemical Thermodynamics

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Section: Sample Characterizationsupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Crystalline anhydrous α,α-trehalose (polymorph β) and crystalline dihydrate α,α-trehalose: A calorimetric study

Pinto¹,

Diogo²,

Ramos³

2006

The Journal of Chemical Thermodynamics

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Consequences of the Preeminent Reactivity of 2-OH in Sucrose: Cyclic Acetalation at 2-OH and 3-OH under Basic Conditions

Giry-Panaud¹,

Descotes²,

Bouchu³

et al. 1999

Eur. J. Org. Chem.

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The reaction of unprotected sucrose with tert‐butyl chloromethyl ketone in dimethylformamide was investigated as a model for the study of the relative reactivity of the various hydroxy groups of sucrose. Besides the monoethers arising from the substitution of the chlorine atom by 2‐OH and 1′‐OH of sucrose, the major product is a tert‐butyl hydroxymethyl 5‐membered ring acetal involving 2‐OH and 3‐OH. The formation of this product illustrates the preeminent reactivity of 2‐OH towards the carbonyl group of the α‐chloromethyl ketone, leading to an intermediate hemiacetalic anion, which can enter by intramolecular acetal formation through an intermediate epoxide.

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ChemInform Abstract: Further Examples of Orthoesterification under Kinetically Controlled Conditions. Application to the Selective Acylation of Sucrose, Maltose, and α,α‐Trehalose.

Bouchra¹,

Gelas²

1998

ChemInform

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Further Examples of Orthoesterification under Kinetically Controlled Conditions.Application to the Selective Acylation of Sucrose, Maltose, and α,α-Trehalose.-The orthoesterification method is applied to sucrose, maltose, and α,α-trehalose in order to obtain selectively acetylated disaccharides. As demonstrated for trehalose (I), reaction with 1,1-dimethoxyethene (II) in DMF affords the orthoester (III) in good yield. Acetylation and hydrolytic cleavage of the orthoester bridges give the polyacetyl disaccharide (VII) which is protected at positions different to the product of conventional acetylation. -(BOUCHRA, M.; GELAS, J.; Carbohydr. Res. 305 (1997) 1, 17-25; Ec. Natl. Super. Chim. Clermont-Ferrand, F-63174 Aubiere, Fr.; EN)

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Further examples of orthoesterification under kinetically controlled conditions application to the selective acylation of sucrose, maltose and α,α-trehalose

Cited by 7 publications

References 11 publications

Crystalline anhydrous α,α-trehalose (polymorph β) and crystalline dihydrate α,α-trehalose: A calorimetric study

Crystalline anhydrous α,α-trehalose (polymorph β) and crystalline dihydrate α,α-trehalose: A calorimetric study

Consequences of the Preeminent Reactivity of 2-OH in Sucrose: Cyclic Acetalation at 2-OH and 3-OH under Basic Conditions

ChemInform Abstract: Further Examples of Orthoesterification under Kinetically Controlled Conditions. Application to the Selective Acylation of Sucrose, Maltose, and α,α‐Trehalose.

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