Glycosidation of 3,4,6-Tri-<i>O</i>-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-<i>C</i>-(β-Methyl)Methylene Glycosides

Feit, Ben‐Ami; Kelson, Idil Kasuto; Gerull, Anke; Abramson, Sarah; Schmidt, Richard R.

doi:10.1080/07328300008544109

Cited by 11 publications

(10 citation statements)

References 20 publications

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“…The corresponding formyl lactal 8 was obtained in 56% yield, whereas a 37% yield was obtained using classical Vilsmeier−Haack conditions (Scheme 3). 20 With respect to the reaction mechanism, we propose one similar to the classical POCl 3 -promoted Vilsmeier−Haack formylation but with a structurally different formylating agent (Scheme 4). 15,19a Isolated yield of 2 after column chromatography.…”

Section: ■ Introductionmentioning

confidence: 99%

Use of XtalFluor-E as an Alternative to POCl₃ in the Vilsmeier–Haack Formylation of C-2-Glycals

et al. 2018

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Section: ■ Introductionmentioning

confidence: 99%

Use of XtalFluor-E as an Alternative to POCl₃ in the Vilsmeier–Haack Formylation of C-2-Glycals

et al. 2018

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“…Feit and co‐workers16 have also recently extended this reaction to disaccharide glycals, in the form of hexa‐ O ‐benzyl lactal 15a and hexa‐ O ‐methyl lactal ( 15b ). The desired formyl glycals 16a and 16b were obtained in moderate yields (Scheme ).…”

Section: Syntheses Of 2‐c‐formyl Glycalsmentioning

confidence: 99%

“…Feit and co‐workers16 have recently reported the synthesis of 2‐ C ‐(β‐methyl)methylene glycosides from the 2‐ethenyl‐ D ‐glucal 38 , in turn obtained in 78% yield by Wittig−type methylenation of 2‐ C ‐formyl glycals 10b with methyl triphenylphosphonium bromide in the presence of n ‐butyllithium as a base. Glycal 38 , on treatment with alcohols (including free OH groups of sugars) in the presence of catalytic amounts of triphenylphosphonium bromide, underwent electrophilic addition to afford the 2‐ C ‐(β‐methyl)methylene glycosides 39 .…”

Section: Syntheses Of 2‐c‐formyl Glycalsmentioning

confidence: 99%

“…Glycal 38 , on treatment with alcohols (including free OH groups of sugars) in the presence of catalytic amounts of triphenylphosphonium bromide, underwent electrophilic addition to afford the 2‐ C ‐(β‐methyl)methylene glycosides 39 . A variety of other nucleophiles (nitrogen and sulfur) have also been used in this reaction (Scheme ) 16. The authors have also synthesized a variety of other C ‐2‐vinyl glycals and C ‐2‐butadienyl glycals.…”

Section: Syntheses Of 2‐c‐formyl Glycalsmentioning

confidence: 99%

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2‐C‐Formyl Glycals: Emerging Chiral Synthons in Organic Synthesis

Ramesh

Balasubramanian²

2003

Eur J Org Chem

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Naturally occurring carbohydrates and their derivatives have been useful during the last few decades as “chiral pool” constituents in the enantioselective synthesis of biologically active natural and non‐natural products. The ready availability of a wide range of carbohydrates in nature and their multichiral architecture, coupled with their well defined stereochemistry, make them attractive starting materials in organic synthesis. The synthesis of key intermediates by incorporation of suitable functional groups onto carbohydrates, which can then be further exploited, has always been a challenging task. In this context, 2‐C‐formyl glycals, a new class of carbohydrates incorporating an α,β‐unsaturated carbonyl system, have recently emerged as potential synthons for numerous organic transformations. Four different syntheses of 2‐C‐formyl glycals have been reported so far. However, the importance of 2‐C‐formyl glycals has become well established after our development of a more general, one‐step synthesis, employing the well known Vilsmeier−Haack reaction. Synthetic transformations of these 2‐C‐formyl glycals have resulted in a variety of new compounds of significant synthetic and biological interest. 2‐C‐Formyl glycals have been shown to be ideal substrates for chemo‐, regio‐ and stereoselective glycosidation, nucleophilic addition/substitution and cycloaddition reactions. The reported syntheses and applications of these important “chiral intermediates” are presented. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…(iii) and (iv)). 76, 77 When a cyclic diacetal is used, it is possible to transform only one of the two possible acetal moieties (Scheme 9, eqns. (v)-(vii)).…”

Section: From Sulfinic Acids and Enol Ethers Or Acetalsmentioning

confidence: 99%

α-Oxy sulfones and sulfoximines: versatile intermediates

Chemla

2002

J. Chem. Soc., Perkin Trans. 1

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Glycosidation of 3,4,6-Tri-O-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-C-(β-Methyl)Methylene Glycosides

Cited by 11 publications

References 20 publications

Use of XtalFluor-E as an Alternative to POCl₃ in the Vilsmeier–Haack Formylation of C-2-Glycals

Use of XtalFluor-E as an Alternative to POCl₃ in the Vilsmeier–Haack Formylation of C-2-Glycals

2‐C‐Formyl Glycals: Emerging Chiral Synthons in Organic Synthesis

α-Oxy sulfones and sulfoximines: versatile intermediates

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Glycosidation of 3,4,6-Tri-O-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-C-(β-Methyl)Methylene Glycosides

Cited by 11 publications

References 20 publications

Use of XtalFluor-E as an Alternative to POCl3 in the Vilsmeier–Haack Formylation of C-2-Glycals

Use of XtalFluor-E as an Alternative to POCl3 in the Vilsmeier–Haack Formylation of C-2-Glycals

2‐C‐Formyl Glycals: Emerging Chiral Synthons in Organic Synthesis

α-Oxy sulfones and sulfoximines: versatile intermediates

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Product

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Use of XtalFluor-E as an Alternative to POCl₃ in the Vilsmeier–Haack Formylation of C-2-Glycals

Use of XtalFluor-E as an Alternative to POCl₃ in the Vilsmeier–Haack Formylation of C-2-Glycals