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. 2010 Nov 17;66(Pt 12):o3217-8.
doi: 10.1107/S1600536810046921.

6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl-idene-d-galacto-pyran-ose

Bogdan Doboszewski, Paulo R da Silva, Alexander Y Nazarenko, Victor N Nemykin

6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl-idene-d-galacto-pyran-ose

Bogdan Doboszewski et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The title compound, C(19)H(30)O(9), was prepared by substitution at the C6 position in 1,2;3,4-di-O-isopropyl-idene-6-O-trifluoro-methane-sulfonyl-d-galactose using sodium eth-oxy-malonate in dimethyl-formamide. The conformation is skew-boat (0)S(2), slightly distorted towards boat B(2,5). The inflexible pyran-ose structure makes the title compound a suitable inter-mediate for further synthetic work by keeping stereogenic carbon atoms safe from inversion. Several short intra-molecular C-H⋯ O contacts may stabilize the conformation of the mol-ecule. Inter-molecular C-H⋯O inter-actions also occur.

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Figures

Fig. 1.
Fig. 1.
The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
Fig. 2.
Fig. 2.
Conformation of the six-membered ring: mean plane drawn through C1—C3—C4—C5.
Fig. 3.
Fig. 3.
Conformation of the five-membered isopropylidene ring: plane through C1 C2 C6 O2.
Fig. 4.
Fig. 4.
Conformation of the five-membered isopropylidene ring: plane through C3 C9 O5 C4.
Fig. 5.
Fig. 5.
Synthetic route towards the title compound.
See this image and copyright information in PMC

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