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Peracetylated α-d-glucopyranosyl fluoride and peracetylated α-maltosyl fluoride
- Publication Year :
- 2010
- Publisher :
- International Union of Crystallography, 2010.
-
Abstract
- The X-ray analyses of 2,3,4,6-tetra-O-acetyl-α-d-glucopyran­osyl fluoride, C14H19FO9, (I), and the corresponding maltose derivative 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-d-glucopyran­osyl fluoride, C26H35FO17, (II), are reported. These add to the series of published α-glyco­syl halide structures; those of the peracetyl­ated α-glucosyl chloride [James & Hall (1969 ▶). Acta Cryst. A25, S196] and bromide [Takai, Watanabe, Hayashi & Watanabe (1976 ▶). Bull. Fac. Eng. Hokkaido Univ. 79, 101–109] have been reported already. In our structures, which have been determined at 140 K, the glycopyranosyl ring appears in a regular 4 C 1 chair conformation with all the substituents, except for the anomeric fluoride (which adopts an axial orientation), in equatorial positions. The observed bond lengths are consistent with a strong anomeric effect, viz. the C1—O5 (carbohydrate numbering) bond lengths are 1.381 (2) and 1.381 (3) Å in (I) and (II), respectively, both significantly shorter than the C5—O5 bond lengths, viz. 1.448 (2) Å in (I) and 1.444 (3) Å in (II).
- Subjects :
- Models, Molecular
Anomer
Magnetic Resonance Spectroscopy
Anomeric effect
Molecular Structure
Stereochemistry
Chemistry
Organic Compounds
Cyclohexane conformation
Halide
Acetylation
Stereoisomerism
General Medicine
Nuclear magnetic resonance spectroscopy
Crystallography, X-Ray
Medicinal chemistry
General Biochemistry, Genetics and Molecular Biology
Bond length
chemistry.chemical_compound
Glucose
Bromide
Carbohydrate Conformation
Maltose
Fluoride
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....bec96bb79f59b0019d45213c72c76552