Abstract
In the title compound, C12H19NO6, the six-membered 1,3-dioxane ring adopts a chair-like conformation. The seat of this chair, containing two O atoms, is essentially planar, with a maximum deviation of 0.0021 (12) Å. The five-membered oxolane ring cis-fused to the 1,3-dioxane ring adopts an envelope form. The bridgehead C atom at the flap, which is bonded to the tetra-substituted C atom of the oxolane ring, deviates from the mean plane of other ring atoms by 0.539 (4) Å. In the crystal, classical O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a sheet structure enclosing an R 4 (4)(24) graph-set motif. Weak inter-molecular C-H⋯O inter-actions support the sheet formation.
Highlights
In the title compound, C12H19NO6, the six-membered 1,3-dioxane ring adopts a chair-like conformation
Sphingofungin F [systematic name: (2S,3R,4R,5S,E)-2amino-3,4,5-trihydroxy-2-methyl-14-oxoicos-6-enoic acid] was isolated from the fermentation broth of Paecilomyces variotii by Horn et al (1992)
The title compound, which is equivalent to the hydrophilic part with correct stereochemistry, was provided in the total synthesis of sphingofungin F (Tsuzaki et al, 2015)
Summary
Sphingofungin F [systematic name: (2S,3R,4R,5S,E)-2amino-3,4,5-trihydroxy-2-methyl-14-oxoicos-6-enoic acid] was isolated from the fermentation broth of Paecilomyces variotii by Horn et al (1992). It shows antifungal activity by inhibition of the serine palmitoyltransferase to suppress the early step of biosynthesis of the sphingosines (Zweerink et al., 1992). The structure of sphingofungin F features a hydrophilic. -disubstituted -amino acid moiety possessing four contiguous stereocenters, connected to a hydrophobic carbon chain by E-olefin. The title compound, which is equivalent to the hydrophilic part with correct stereochemistry, was provided in the total synthesis of sphingofungin F (Tsuzaki et al, 2015)
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