E.i. mass spectrometry of per-O-benzylated 1,3-, 1,2-, and 1,6-anhydropyranoses

Electron impact mass spectra (70 eV) were generated for tri‐O‐benzyl‐D‐glucal and six XC6H5S substituted 3,4,6‐tri‐O‐benzyl‐β‐C‐glucosides which had been modified at C(2) by the introduction of an XC6H4S fragment (where X = CH3 or CI) in an effort to understand better fragmentation processes for the structural characterization of this important class of compounds. The model compounds which were synthesized were glucoside derivatives of CH2CHO, C(CH3)2CHO, , C6H5 and CN. For all O‐benzylated compounds, the benzyl moiety was the base ion; however, the molecule ion of each modified glucoside was significantly abundant. A characteristic feature of S‐containing C‐glucosides was an abundant CH3C6H5SCHCHCH2 ion at m/z 163. Fragmentation of these C‐glucosides was interpreted in terms of positive charge localization on the molecule ion according to rules for normal carbohydrates. Knowledge of the fragmentation on the S‐containing C‐glucosides should be useful for the characterization of additional new analogues.

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Mass spectral characterization of 3,4,6‐tri‐O‐benzyl‐β‐C‐glucopyranosides containing XC₆H₄S substituents of C(2)

Rozynov

Liukkonen

Carlson

et al. 1994

Org. Mass Spectrom.

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Synthesis, conformational analysis, and the glycosidic coupling reaction of substituted 2,7-dioxabicyclo[4.1.0]heptanes: 1,2-anhydro-3,4-di-O-benzyl-β-l- and β-d-rhamnopyranoses

Chen

Kong

Cao³

1993

Carbohydrate Research

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Synthesis and conformation of 1,2-anhydro,3,4-6-tri-O-benzyl-β-d-talopyranose

Liu¹,

Kong²,

Cao³

1993

Carbohydrate Research

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E.i. mass spectrometry of per-O-benzylated 1,3-, 1,2-, and 1,6-anhydropyranoses

Cited by 7 publications

References 11 publications

Mass spectral characterization of 3,4,6‐tri‐O‐benzyl‐β‐C‐glucopyranosides containing XC₆H₄S substituents of C(2)

Mass spectral characterization of 3,4,6‐tri‐O‐benzyl‐β‐C‐glucopyranosides containing XC₆H₄S substituents of C(2)

Synthesis, conformational analysis, and the glycosidic coupling reaction of substituted 2,7-dioxabicyclo[4.1.0]heptanes: 1,2-anhydro-3,4-di-O-benzyl-β-l- and β-d-rhamnopyranoses

Synthesis and conformation of 1,2-anhydro,3,4-6-tri-O-benzyl-β-d-talopyranose

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E.i. mass spectrometry of per-O-benzylated 1,3-, 1,2-, and 1,6-anhydropyranoses

Cited by 7 publications

References 11 publications

Mass spectral characterization of 3,4,6‐tri‐O‐benzyl‐β‐C‐glucopyranosides containing XC6H4S substituents of C(2)

Mass spectral characterization of 3,4,6‐tri‐O‐benzyl‐β‐C‐glucopyranosides containing XC6H4S substituents of C(2)

Synthesis, conformational analysis, and the glycosidic coupling reaction of substituted 2,7-dioxabicyclo[4.1.0]heptanes: 1,2-anhydro-3,4-di-O-benzyl-β-l- and β-d-rhamnopyranoses

Synthesis and conformation of 1,2-anhydro,3,4-6-tri-O-benzyl-β-d-talopyranose

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Product

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Mass spectral characterization of 3,4,6‐tri‐O‐benzyl‐β‐C‐glucopyranosides containing XC₆H₄S substituents of C(2)

Mass spectral characterization of 3,4,6‐tri‐O‐benzyl‐β‐C‐glucopyranosides containing XC₆H₄S substituents of C(2)