Nuclear Magnetic Resonance Spectral Studies on some Anhydro Furanose Derivatives

Hiraoka, Tetsuo; Iwashige, Tadahiro; Iwai, Issei

doi:10.1248/cpb.13.285

Cited by 6 publications

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“…Other Conformational Features of 5 − 8. The preferred conformation of the five-membered ring in 2,3-anhydrofuranosides has been the topic of some discussion, , and our calculations shed light on this issue. The epoxide ring in 5 − 8 necessitates that the furan ring can only adopt either the E O or O E conformer.…”

Section: Resultsmentioning

confidence: 78%

Sensitivity of ¹J_C1_-_H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides

2001

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The magnitude of the one-bond coupling constant between C(1) and H(1) in 2,3-anhydro-O-furanosides has been shown to be sensitive to the stereochemistry at the anomeric center. A panel of 24 compounds was studied and in cases where the anomeric hydrogen is trans to the epoxide moiety, (1)J[C(1)-H(1)] = 163-168 Hz; and when this hydrogen is cis to the oxirane ring, ((1)J[C(1)-H(1)] = 171-174 Hz. In contrast, for 2,3-anhydro-S-glycosides, the size of the (1)J[C(1)-H(1)] is not sensitive to C(1) stereochemistry. Computational studies on all four methyl 2,3-anhydro-O-furanosides (5-8) demonstrated that (1)J[C(1)-H(1)] was inversely proportional to the length of the C(1)-H(1) bond. A previously reported equation, which relates C(1)-H(1) bond distance and atomic charges to (1)J[C(1)-H(1)] magnitudes, could be used to accurately predict the J values in the alpha-lyxo (5) and beta-ribo (8) isomers. In contrast, with the beta-lyxo (6) and alpha-ribo isomers (7), this equation underestimated the size of these coupling constants by 10-20 Hz.

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Section: Resultsmentioning

confidence: 78%

Sensitivity of ¹J_C1_-_H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides

2001

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Nitration of furan derivatives with acetyl nitrate

Lolya

Venter

Лиепиньш

et al. 1975

Chem Heterocycl Compd

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Carbon-13 nuclear magnetic resonance spectra of carbohydrate oxirane derivatives

Kwan

Vyas

Szarek

1979

Carbohydrate Research

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Nuclear Magnetic Resonance Spectral Studies on some Anhydro Furanose Derivatives

Cited by 6 publications

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Sensitivity of ¹J_C1_-_H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides

Sensitivity of ¹J_C1_-_H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides

Nitration of furan derivatives with acetyl nitrate

Carbon-13 nuclear magnetic resonance spectra of carbohydrate oxirane derivatives

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Nuclear Magnetic Resonance Spectral Studies on some Anhydro Furanose Derivatives

Cited by 6 publications

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Sensitivity of 1JC1-H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides

Sensitivity of 1JC1-H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides

Nitration of furan derivatives with acetyl nitrate

Carbon-13 nuclear magnetic resonance spectra of carbohydrate oxirane derivatives

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Product

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Sensitivity of ¹J_C1_-_H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides

Sensitivity of ¹J_C1_-_H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides