Sc(OTf) 3 -catalyzed acetolysis of 1,6-anhydro-β-hexopyranoses and solvent-free per-acetylation of hexoses

Lee, Jinq‐Chyi; Tai, Cheng‐An; Hung, Shang‐Cheng

doi:10.1016/s0040-4039(01)02253-5

Cited by 84 publications

(32 citation statements)

References 45 publications

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“…Some pyridine derivatives such as 4-(N, N)-dimethylaminopyridine (DMAP) and 4-(1-pyrrolidino) pyridine as a co-catalyst can speed up this transformation [3]. Besides, Lewis acids such as ZnCl 2 [4], Sc(OTf) 3 [5], Cu(OTf) 2 [6], InCl 3 [7], BF 3 ⋅OEt 2 [8], etc. have also been reported as efficient catalysts for carbohydrate acetylation with acetic anhydride.…”

Section: Introductionmentioning

confidence: 99%

Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O

Shi¹,

Zhang²,

Fu³

et al. 2006

LOC

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Section: Introductionmentioning

confidence: 99%

Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O

Shi¹,

Zhang²,

Fu³

et al. 2006

LOC

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“…The susceptibility of the anhydro-ring to attack by sulfur nucleophiles from reagents such as TMSSMe and TMSSPh in the presence of trimethylsilyl triflate (TMSOTf) or ZnI 2 to generate thioglycosides had been demonstrated (33,48). To open the anhydro-ring, we developed the metal triflate-mediated acetolysis that leaves a labile acetyl group at the anomeric center (49). In one example (50), the fully protected 13, generated upon benzylation of 9, was treated with Cu(OTf) 2 and Ac 2 O to deliver the diacetate 14 in excellent yield (Scheme 2).…”

Section: B-1 Access To L-idose/idoa Derivativesmentioning

confidence: 99%

Chemical Synthesis of Oligosaccharides Based on Heparin and Heparan Sulfate

Zulueta

Lin

Hung

2013

TIGG

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Heparin and heparan sulfate (HS) are complex polysaccharides that mediate and modulate the activity of numerous proteins. These proteins associate with the sugar's repeating disaccharide backbone, which is decorated with diverse sulfation patterns. Knowledge of the molecular details of these interactions may allow the development of new forms of diagnostic and therapeutic agents. Chemical syntheses of heparin-and HS-based oligosaccharides are vital in accessing the well-defined materials required by structure-activity relationship evaluations. These synthetic efforts, however, are confronted with several challenges such as access to the rare L-idose/L-iduronic acid derivatives, α-stereoselectivity in glucosaminylation, the manner of chain elongation, the selection and manipulation of protecting groups including the introduction of sulfonate groups at defined positions, and the efficient generation of compounds that are diverse enough to represent the natural heparin and HS chains. This review focuses on our achievements in addressing these concerns together with concise descriptions of the collective solutions that have been developed thus far. We also briefly highlight the results of biological assays involving our sugar constructs.

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“…Metal triflates used for acetylation of alcohols and phenols are gadolinium triflate (22), aluminum triflate (23), and scandium triflate (24,25). TaCl 5 (26) , InCl 3 (27) , and ZrOCl 2 ×8H 2 O (28) are frequently used metal halides for acetylation.…”

Section: Introductionmentioning

confidence: 99%

Formylation and acetylation of alcohols using Amberlyst-15^®as a recyclable heterogeneous catalyst

Singh

Bhanage

Nagarkar

2012

Green Chemistry Letters and Reviews

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Formylation of alcohols with ethyl formate in the presence of solid acidic resin Amberlyst-15 as a catalyst was carried out. Good to excellent yields of products were obtained. The catalyst also works for the acetylation of alcohols with ethyl acetate at reflux temperature. Simple work-up, reusability, nontoxicity, and stability of the catalyst are the advantages of this work as compared to conventional protocols.

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Sc(OTf) 3 -catalyzed acetolysis of 1,6-anhydro-β-hexopyranoses and solvent-free per-acetylation of hexoses

Cited by 84 publications

References 45 publications

Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O

Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O

Chemical Synthesis of Oligosaccharides Based on Heparin and Heparan Sulfate

Formylation and acetylation of alcohols using Amberlyst-15^®as a recyclable heterogeneous catalyst

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Sc(OTf) 3 -catalyzed acetolysis of 1,6-anhydro-β-hexopyranoses and solvent-free per-acetylation of hexoses

Cited by 84 publications

References 45 publications

Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O

Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O

Chemical Synthesis of Oligosaccharides Based on Heparin and Heparan Sulfate

Formylation and acetylation of alcohols using Amberlyst-15®as a recyclable heterogeneous catalyst

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Formylation and acetylation of alcohols using Amberlyst-15^®as a recyclable heterogeneous catalyst