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2-C-Azido­methyl-2-de­oxy-3,4-O-isopropyl­idene-d-ribono-1,5-lactone

✍ Scribed by Punzo, Francesco ;Watkin, David J. ;Jenkinson, Sarah F. ;da Cruz, Filipa P. ;Fleet, George W. J.

Publisher
International Union of Crystallography
Year
2005
Tongue
English
Weight
266 KB
Volume
62
Category
Article
ISSN
1600-5368

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✦ Synopsis

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 molecules in the asymmetric unit.

📜 SIMILAR VOLUMES

2-Azido-2-de­oxy-2,4-C-dimethyl-3,4-O-is
2-Azido-2-de­oxy-2,4-C-dimethyl-3,4-O-isopropyl­idene-l-ribono-1,5-lactone
✍ Booth, Kathrine V. ;Watkin, David J. ;Jenkinson, Sarah F. ;Fleet, George W. J. 📂 Article 📅 2007 🏛 International Union of Crystallography 🌐 English ⚖ 308 KB

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.

2-Azido-2-deoxy-3,4-O-iso­propyl­idene-2
2-Azido-2-deoxy-3,4-O-iso­propyl­idene-2-C-methyl-d-ribono-1,5-lactone
✍ Punzo, Francesco ;Watkin, David J. ;Jenkinson, Sarah F. ;Cruz, Filipa P. da ;Fle 📂 Article 📅 2005 🏛 International Union of Crystallography 🌐 English ⚖ 250 KB

Single-crystal X-ray study T = 120 K Mean '(C±C) = 0.004 A Ê R factor = 0.045 wR factor = 0.102 Data-to-parameter ratio = 11.0 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

3,4-O-Isopropyl­idene-2-C-methyl-d-arabi
3,4-O-Isopropyl­idene-2-C-methyl-d-arabinono-1,5-lactone
✍ Punzo, Francesco ;Watkin, David J. ;Jenkinson, Sarah F. ;Fleet, George W. J. 📂 Article 📅 2004 🏛 International Union of Crystallography 🌐 English ⚖ 250 KB

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.

5-O-tert-Butyl­diphenyl­silyl-2-C-hydrox
5-O-tert-Butyl­diphenyl­silyl-2-C-hydroxy­methyl-2,3-O-isopropyl­idene-2′-O-trifluoro­methane­sulfonyl-d-ribono-1,4-lactone
✍ Simone, Michela ;Fleet, George W. J. ;Watkin, David J. 📂 Article 📅 2007 🏛 International Union of Crystallography 🌐 English ⚖ 435 KB

The title compound, C~26~H~31~F~3~O~8~SSi, provides a unique example of the crystal structure of an organic trifluoromethanesulfonate attached to a primary C atom. The absolute configuration is determined by the use of D-ribose as the starting material.

2-De­oxy-2-fluoro-2-C-methyl-d-ribono-1,
2-De­oxy-2-fluoro-2-C-methyl-d-ribono-1,4-lactone (fluoro­methyl­rib)
✍ Parker, Samuel ;Watkin, David ;Mayes, Benjamin ;Storer, Richard ;Jenkinson, Sara 📂 Article 📅 2006 🏛 International Union of Crystallography 🌐 English ⚖ 297 KB

The relative stereochemistry of the fluoro substituent (as __ribo__) and the ring size of the lactone (as five) in the title compound, C~6~H~9~FO~4~, have been established by X-ray crystallographic analysis.