1. 3,4,6-Tri- O-acetyl-1,2- O-[1-( exo-ethoxy)ethylidene]-β- d-mannopyranose 0.11-hydrate.
- Author
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Liu, Ya-Ling, Zou, Pei, Wu, Hao, Xie, Min-Hao, and Luo, Shi-Neng
- Subjects
ACETYL compounds ,ETHOXY compounds ,PYRANOSES ,HYDRATES ,MOLECULAR probes ,HYDROGEN bonding ,POSITRON emission tomography ,CRYSTAL structure - Abstract
The title compound, C
16 H24 O10 ·0.11H2 O, is a key intermediate in the synthesis of 2-deoxy-2-[18 F]fluoro- d-glucose (18 F-FDG), which is the most widely used molecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent molecules ( A and B) in the asymmetric unit, with closely comparable geometries. The pyranose ring adopts a4 C1 conformation [Cremer-Pople puckering parameters: Q = 0.553 (2) Å, θ = 16.2 (2)° and ϕ = 290.4 (8)° for molecule A, and Q = 0.529 (2) Å, θ =15.3 (3)° and ϕ = 268.2 (9)° for molecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the ethoxy group exo to the mannopyranose ring. The asymmetric unit also contains one water molecule with a refined site-occupancy factor of 0.222 (8), which bridges between molecules A and B via O-H...O hydrogen bonds. [ABSTRACT FROM AUTHOR]- Published
- 2012
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