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2,3-O-Isopropyl­idene-l-apiono-1,4-lactone [(3S,4S)-3,4-dihydr­oxy-4-(hydroxy­methyl)-3,4-di-O-isopropyl­idene-4,5-dihydro­furan-2(3H)-one]

✍ Scribed by Best, Daniel ;Jenkinson, Sarah F. ;Watkin, David J. ;Booth, Kathrine V. ;Fleet, George W. J.


Publisher
International Union of Crystallography
Year
2007
Tongue
English
Weight
197 KB
Volume
63
Category
Article
ISSN
1600-5368

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The relative configuration at C-2 of 2,4-dimethyl-3,4-__O__-isopropylidene-L-arabinono lactone, C~10~H~16~O~5~, which exists in the boat form, was unequivocally established by X-ray crystallographic analysis. The absolute configuration was determined by the use of 2-__C__-methyl-D-ribonolactone as a

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Single-crystal X-ray study T = 190 K Mean '(C±C) = 0.002 A Ê R factor = 0.031 wR factor = 0.078 Data-to-parameter ratio = 12.0 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

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The title compound, C 21 H 22 O 2 , has the exocyclic C C double bond in an E configuration. The isopropyl group is attached in an axial position to the cyclohexenone ring.

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The relative configuration of the title lactone, C 10 H 15 N 3 O 4 , a compound of value in the synthesis of complex pyrrolidines, was determined by X-ray crystallographic analysis.

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✍ Punzo, Francesco ;Watkin, David J. ;Jenkinson, Sarah F. ;da Cruz, Filipa P. ;Fle 📂 Article 📅 2005 🏛 International Union of Crystallography 🌐 English ⚖ 266 KB

X-ray crystallographic analysis firmly establishes the ribo stereochemistry and the unusual boat conformation of the title branched carbon chain lactone, C 9 H 13 N 3 O 4 , arising from an unexpected rearrangement in the nucleophilic substitution of a trifluoromethanesulfonate. There are two molecul