The Synthesis of Rare Sugars

Brimacombe, J. S.

doi:10.1002/anie.196904011

Cited by 43 publications

(9 citation statements)

References 58 publications

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“…Reviews (46,54,55) list little reported information on use of strong bases (e.g., potassium-ter£-butoxide, sodium acetate) in oxidations with methyl sulfoxide; however, sodium bicarbonate was used as an acid acceptor in the oxidation of aromatic halides or tosylates (46). The procedure below describes the use of a mixture of methyl sulfoxide, acetic anhydride and potassium terf-butoxide for acetylation of a sugar or inosose phenyl hydrazone to yield a ^-elimination product.…”

Section: Methodsmentioning

confidence: 99%

Electron Spin Resonance Studies of Chemical Changes of Phenylhydrazones and Osazones in Alkaline Solution

Fatiadi

1973

Carbohydrates in Solution

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Treatment of a solution of a sugar phenylhydrazone or osazone in methyl sulfoxide with potassium tert-butoxide and a trace of oxygen at room temperature gives products that have a three-line electron spin resonance (ESR) spectrum characteristic of a nitroxide radical The apparent fragmentation of the phenylhydrazine moiety under reaction conditions used does not show evidence of any paramagnetic species derived from glyoxal bis(phenylhydrazone). The latter had been reported to be the product of degradation of the sugar phenylhydrazones under more vigorous alkaline treatment. Some inosose phenylhydrazones in alkaline methyl sulfoxide solution produce stable radical-anions in which the phenylhydrazine moiety remains intact. A free radical mechanism is advanced to account for the β-elimination reactions of the sugar phenylhydrazones under mildly basic conditions.

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Section: Methodsmentioning

confidence: 99%

Electron Spin Resonance Studies of Chemical Changes of Phenylhydrazones and Osazones in Alkaline Solution

Fatiadi

1973

Carbohydrates in Solution

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“…It has been shown that carbohydrate molecules possessing the enone functionality are the preferred precursors for the synthesis of branched-chain and rare sugars. [17][18][19][20][21][22] However enones are key intermediates in the synthesis of monosaccharides from non-carbohydrate precursors. 23 The stereochemical relationships at C-2, C-3 and C-4 are determined by a wise choice of reaction sequences: reduction of ketone and cishydroxylation or epoxidation.…”

Section: Anmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of New Alkyl 2-Azido-2,3-Dideoxy-α-D-Lixo-Hexopyranosides From α,β-Unsaturated Sugar Enones and Sodium Azide

Silva¹,

Freitas²,

Souza³

et al. 2019

Rev. Virtual Quim.

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Síntese e Atividade Citotóxica de Novos Alquil 2-azido-2,3-dideoxi-α-D-Lixo-hexopiranosídeos Obtidos a Partir de Enonas α,β-Insaturados e Azida de Sódio Resumo: Este trabalho descreve a síntese de cinco novos alquil 2-azido-2,3-dideoxi-α-D-lixohexopiranosídeo (7a-e) a partir de enonas α,β-insaturados e azida de sódio em presença de ácido acético. Um intermediário chave, alquil 2-azido-dideoxi-α-D-treo-hexopiranosídeo-4-ulose (6a-e), foi utilizado para obter os compostos 7a-e. Os compostos 7a-e foram obtidos em bons rendimentos (65-78 %). As estruturas dos compostos sintetizados foram elucidadas usando espectrometria de infravermelho, RMN de 1 H e 13 C e análise elementar. As suas atividades antiproliferativas foram avaliadas contra quatro diferentes linhagens celulares humanas que também são descritas neste trabalho. O composto 7c exibiu uma boa atividade citotóxica contra as linhagens celulares estudadas HL-60, NCI H292, MCF-7 e HEP com valores de 6,8 µg / mL, 9,9 µg / mL, 12,1 µg / mL e 5,1 µg / mL, respectivamente.

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“…109 Os cetoaçúcares α,β-insaturados são excelentes materiais de partida para a síntese de aminoaçúcares. 110 Em 1982, Holder 111 fez uma revisão destas hexenopiranosiduloses.…”

Section: Síntese De Aminoaçúcares De Cadeia Ramificada a Partir De Ceunclassified

Avanços Recentes Na Química Dos Aminoaçúcares: Ocorrência, Biossíntese, Síntese E Aplicação

Moura

Guimarães

Lima

et al. 2019

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RECENT ADVANCES IN CHEMISTRY OF AMINO SUGARS: OCCURRENCE, BIOSYNTHESIS, SYNTHESIS AND APPLICATION. Amino sugars are chemical compounds that have a sugar backbone, in which one of the hydroxyl groups is replaced by an amino group. Derivatives of amine-containing sugars, such as N-acetylglucosamine, are also considered amino sugars. The synthetic introduction of amino functionalities in a regio-and stereoselective manner ontosugar scaffolds represents a substantial challenge. Most of the modern methods for the preparation of 1-, 2-and 3-amino sugars are those starting from glycals, 2,3-unsaturated O-glycosides epoxy-sugars, keto-sugars among others. This review summarizes recent developments in the current state of knowledge concerning the occurrence, biosynthesis, synthesis and application of amino sugars.

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The Synthesis of Rare Sugars

Cited by 43 publications

References 58 publications

Electron Spin Resonance Studies of Chemical Changes of Phenylhydrazones and Osazones in Alkaline Solution

Electron Spin Resonance Studies of Chemical Changes of Phenylhydrazones and Osazones in Alkaline Solution

Synthesis and Cytotoxic Activity of New Alkyl 2-Azido-2,3-Dideoxy-α-D-Lixo-Hexopyranosides From α,β-Unsaturated Sugar Enones and Sodium Azide

Avanços Recentes Na Química Dos Aminoaçúcares: Ocorrência, Biossíntese, Síntese E Aplicação

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