Synthesis of chiral oxepanes and pyrans by 3-O-allylcarbohydrate nitrone cycloaddition (3-OACNC)

Bhattacharjee, Ashoke; Datta, Shreyasi; Chattopadhyay, Partha; Ghoshal, Nanda; Kundu, Asish P.; Pal, Arani; Mukhopadhyay, Ranjan; Chowdhury, Sandip; Bhattacharjya, Anup; Patra, Amarendra

doi:10.1016/s0040-4020(03)00634-3

Cited by 23 publications

(11 citation statements)

References 38 publications

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“…A few reports in the literature deal with seven-membered polyhydroxylated ethers like septanosides (containing an anomeric center) [ 8 ] as well as compounds without an acetal moiety. Known methods for the construction of the seven-membered polyhydroxylated oxacycle, are for instance cycloaddition [ 9 – 11 ] or cyclodehydration of commercially available alcohols [ 12 – 14 ]. The disadvantages of these methods are the lack of selectivity as well as of stereocontrol and hence other routes are needed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Bouché¹,

Kandziora²,

Reißig³

2014

Beilstein J. Org. Chem.

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SummaryNew compounds with carbohydrate-similar structure (carbohydrate mimetics) are presented in this article. Starting from enantiopure nitrones and lithiated TMSE-allene we prepared three 1,2-oxazine derivatives which underwent a highly stereoselective Lewis acid-induced rearrangement to give bicyclic products in good yield. Subsequent reductive transformations delivered a library of new poly(hydroxy)aminooxepane derivatives. The crucial final palladium-catalyzed hydrogenolysis of the 1,2-oxazine moiety was optimized resulting in a reasonably efficient approach to a series of new seven-membered carbohydrate mimetics.

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Section: Introductionmentioning

confidence: 99%

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Bouché¹,

Kandziora²,

Reißig³

2014

Beilstein J. Org. Chem.

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“…Various potential chiral auxiliaries, used for the synthesis of chiral molecules, have been generated from carbohydrates through judicious manipulation of the sugar backbone. Attempts to elaborate the synthetic utility of the INC methodology on sugar-based substrates have resulted in generating carbocycles, heterocycles, bicycles, spirocycles, cyclic ethers, alkaloids, amino acids, nucleosides, iminosugars, pseudosaccharides, enzyme inhibitors, precursors for prostaglandin and tetrodotoxin, and other related molecular entities. Nevertheless, the chemistry utilizing this method continues unabated in constructing complex ring systems.…”

Section: Introductionmentioning

confidence: 99%

Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives

et al. 2014

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Application of intramolecular 1,3-dipolar nitrone cycloaddition reaction on carbohydrate-derived precursors containing an olefin functionality at C-1 or C-3 or C-5 and a nitrone moiety at C-2 or C-3 as appropriate has resulted in the formation of structurally new cycloaddition products containing furanose-fused oxepane, thiepane, azepane, cyclopentane, cycloheptane, tetrahydrofuran, and pyranose-fused tetrahydrofuran rings. The structure and stereochemistry of these products have been characterized by spectral as well as single-crystal X-ray analyses. Two of the compounds have been transformed to the bicyclic nucleoside derivatives applying Vorbrüggen reaction conditions.

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“…19 Selective 4,6-O-isopropylidenation of the resultant tetraols 5-7 with 2-methoxypropene in DMF in the presence of catalytic amounts of TsOH afforded the target diol compounds. The above three steps were processed in a consecutive manner without chromatographic separation of the intermediates, making a much simplified preparation of 8-10.…”

Section: Introductionmentioning

confidence: 99%

Regio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols

Zhang

Liang

Wang

et al. 2007

Carbohydrate Research

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Abstract-A highly regio-and stereoselective anomeric esterification of 3-O-allyl (or benzyl, or benzoyl)-4,6-O-isopropylidene-a,b-D D-glucopyranose with acetyl chloride, or allyl chloroformate, or ethyl chloroformate gave the corresponding 2-OH, 1-b-acetates or -carbonates in excellent yields. The 2-OH, 1-b-acetates were readily converted to the corresponding 2-O-acetylated glucopyranosyl trichloroacetimidates by reaction with trichloroacetonitrile via base promoted acetyl migration, while the 2-OH, 1-b-carbonates were good glycosyl acceptors for the synthesis of (1!2)-linked oligosaccharides.

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Synthesis of chiral oxepanes and pyrans by 3-O-allylcarbohydrate nitrone cycloaddition (3-OACNC)

Cited by 23 publications

References 38 publications

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives

Regio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols

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