Glycosylation of l,4:3,6-dianhydro-d-glucitol (isosorbide)

Claffey, David J.; Casey, Mary; Finan, P. A.

doi:10.1016/j.carres.2004.07.007

Cited by 13 publications

(17 citation statements)

References 13 publications

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“…Isosorbide (1) is an asymmetric V-shaped diol consisting of two fused tetrahydrofuran rings having the cis-arrangement at the ring junction ( Figure 1). [13] In order to carry out our approach, two different protecting groups, i.e. The first one is more accessible whereas the second one is involved in an intramolecular hydrogen bond with the oxygen atom on the neighboring tetrahydrofuran ring.…”

Section: Glycal Synthesismentioning

confidence: 99%

“…The first one is more accessible whereas the second one is involved in an intramolecular hydrogen bond with the oxygen atom on the neighboring tetrahydrofuran ring. [13] In order to carry out our approach, two different protecting groups, i.e. benzyl and acetyl, were selected to protect the hydroxy at C-5 regioselectively.…”

Section: Glycal Synthesismentioning

confidence: 99%

“… 13. C NMR (75 MHz, CDCl 3 ): δ = 29.4 (C-3), 31.8 (C-2Ј), 60.0 (C-1Ј), 65.8 (C-3Ј), 70.1 (C-5), 72.1 (CH 2 Ph), 77.9 (C-6), 81.3 (C-6 a ), 90.6 (C-3 a ), 112.6 (C-2), 128.0 (CH Ar ), 128.0 (CH Ar ), 128.4 (CH Ar ), 137.2 (C Ar ) ppm.…”

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confidence: 99%

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Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives

Lavergne¹,

Molinier²,

Capet³

et al. 2013

Eur J Org Chem

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A set of O-alkylated or O-arylated β-iodo ethers has been synthesized from isosorbide. Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. The key step was the iodoetherification of isosorbide-derived glycals with a variety 1939 Figure 3. ORTEP plot of β-iodo ether 3ak.Scheme 4. Proposed mechanistic pathway for the NIS-mediated addition of alcohol 7k to glycal 4a.www.eurjoc.org

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Section: Glycal Synthesismentioning

confidence: 99%

Section: Glycal Synthesismentioning

confidence: 99%

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Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives

Lavergne¹,

Molinier²,

Capet³

et al. 2013

Eur J Org Chem

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“…Scheme shows the different reactivity based on the geometry of the two hydroxy groups. The hydroxy group of C2 appears to be in the exo orientation, whereas that of C5 appears to be in the endo orientation, because of the fused tetrahydrofuran (THF) cycles (Abenhaïm et al, ; Claffey et al, ; Kumar and Ramachandran, ; Zhu et al, ). The reaction shown in Scheme is used to prepare many compounds such as isosorbide nitrates (used to treat cardiac or vascular disease) and alkyl derivatives (used as solvents in pharmaceutical and cosmetic compositions) (Durand et al, ; Fenouillot et al, ; Lavergne et al, ).…”

Section: Introductionmentioning

confidence: 99%

Selective Syntheses and Properties of Anionic Surfactants Derived from Isosorbide

Cho

Sim

Kim

et al. 2018

J Surfact & Detergents

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Two series of anionic surfactants (endo‐5‐O‐alkyl isosorbide‐2‐O‐propyl sulfonic acid sodium salt and exo‐2‐O‐alkyl isosorbide‐5‐O‐propyl sulfonic acid sodium salt) with straight alkyl chains (hexyl, octyl, decyl, and dodecyl) were synthesized from isosorbide derived from biomass, through steps of allylation, alkylation, and sulfonation. The selectivity and efficiency of the reactions were optimized by adjusting the solvent, catalyst, reactant molar ratio, and temperature. The product 2‐O‐allyl isosorbide was obtained with a yield of 81% and selectivity of 23:1 (endo:exo), and 2‐O‐alkyl isosorbide was obtained with a yield of 72% and selectivity of 24:1 (exo:endo). The synthesized anionic surfactants were characterized using the critical micelle concentration (CMC), surface activity, emulsion stability, foaming height, and the Turbiscan Stability Index. The CMC decreased with increasing alkyl chain length. The properties of endo form and exo form were compared.

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“…Thus, glycosylation of 2,3,4,6-tetra-O-acetyl--D-gluco-pyranosyl, 2,3,4,6-tetra-O-acetyl--D-galactopyranosyl and 2,3,4-tri-O-acetyl--D-xylopyranosyl bromides with 1,4:3,6-dianhydro-D-glucitol have been carried out under Köenigs-Knorr conditions and using the Helferich modification[68]. Regioselectivity towards the C-5 of 1,4:3,6-dianhydro-D-glucitol was observed.The preparation of a galactosyl and mannosyl trisaccharide and of tetrasaccharide -D-Galp-(1 2)--D-Manp-(1 2)--D-Manp-(1 6)--D-ManpOCH 3 63 (Scheme 20) was carried out by a combination of the trichloroacetimidate and Köenigs-Knorr methods…”

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confidence: 99%

Glycosylation Methods in Oligosaccharide Synthesis. Part 1

Robina¹,

Carmona²,

Vargas

2008

COS

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A review dealing with the general aspects of oligosaccharide synthesis including the recent advances in protecting group strategies and anomeric control for stereoselective glycosylations, focusing on the formation of 1,2-cis-glycosides, are presented. Recent examples of the intramolecular aglycon delivery approach and of the remote effect on the stereochemistry of the new glycosidic bond are considered. In this part, updated examples of the use of glycosyl halides, thioglycosides, sulfoxides and phenylselenides as glycosylating agents for oligosaccharide synthesis are also discussed.

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Glycosylation of l,4:3,6-dianhydro-d-glucitol (isosorbide)

Cited by 13 publications

References 13 publications

Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives

Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives

Selective Syntheses and Properties of Anionic Surfactants Derived from Isosorbide

Glycosylation Methods in Oligosaccharide Synthesis. Part 1

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