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(±)-1-{8'-(tert-Butyl-diphenyl-silyloxy-meth-yl)-1',7'-dioxaspiro-[5.5]undecan-2'-yl}uridine.

Choi KW, Brimble MA, Groutso T - Acta Crystallogr Sect E Struct Rep Online (2008)

Bottom Line: Each of the O atoms in the tetra-hydro-pyran rings adopts an axial position on the neighbouring ring.This bis--diaxial conformation is adopted, thus gaining maximum stablization from the anomeric effect.The silyl-protected hydroxy-methyl and uracil substituents adopt equatorial positions on their associated tetra-hydro-pyran rings, thereby minimizing unfavourable steric inter-actions.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Univerisity of Auckland, Private Bag 92019, Auckland, New Zealand.

ABSTRACT
The crystal structure of the title compound, C(30)H(38)N(2)O(5)Si, has been investigated to establish the relative stereochemistry at the spiro ring junction and the two anomeric centres. Each of the O atoms in the tetra-hydro-pyran rings adopts an axial position on the neighbouring ring. This bis--diaxial conformation is adopted, thus gaining maximum stablization from the anomeric effect. The silyl-protected hydroxy-methyl and uracil substituents adopt equatorial positions on their associated tetra-hydro-pyran rings, thereby minimizing unfavourable steric inter-actions. The dimeric (2'R*,6'R*,8'R*)- and (2'S*,6'S*,8'S*)-uridine units are connected to each other across crystallographic inversion centres via inter-molecular N-H⋯O hydrogen bonds.

No MeSH data available.


Related in: MedlinePlus

Molecular packing of racemic uridine units. The dimeric units of opposite chirality, (2'R*,6R'*,8'R*)- and (2'S*,6'S*,8'S*)-uridines are connected to each other by intermolecular hydrogen bonds. Dashed lines represent hydrogen bonds. Most hydrogen atoms that are not involved in hydrogen bonding, have been omitted for clarity. The origin of the unit cell is labelled as O while cell axes are labelled as a (red), b (green) and c (blue), respectively. [Symmetry code: (ii) 1/2 - x, -1/2 + y, 1/2 - z; (iii) 1/2 + x, 3/2 - y, 1/2 + z; (iv) -x + 1, -y + 1, -z + 1.]
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Fap2: Molecular packing of racemic uridine units. The dimeric units of opposite chirality, (2'R*,6R'*,8'R*)- and (2'S*,6'S*,8'S*)-uridines are connected to each other by intermolecular hydrogen bonds. Dashed lines represent hydrogen bonds. Most hydrogen atoms that are not involved in hydrogen bonding, have been omitted for clarity. The origin of the unit cell is labelled as O while cell axes are labelled as a (red), b (green) and c (blue), respectively. [Symmetry code: (ii) 1/2 - x, -1/2 + y, 1/2 - z; (iii) 1/2 + x, 3/2 - y, 1/2 + z; (iv) -x + 1, -y + 1, -z + 1.]


(±)-1-{8'-(tert-Butyl-diphenyl-silyloxy-meth-yl)-1',7'-dioxaspiro-[5.5]undecan-2'-yl}uridine.

Choi KW, Brimble MA, Groutso T - Acta Crystallogr Sect E Struct Rep Online (2008)

Molecular packing of racemic uridine units. The dimeric units of opposite chirality, (2'R*,6R'*,8'R*)- and (2'S*,6'S*,8'S*)-uridines are connected to each other by intermolecular hydrogen bonds. Dashed lines represent hydrogen bonds. Most hydrogen atoms that are not involved in hydrogen bonding, have been omitted for clarity. The origin of the unit cell is labelled as O while cell axes are labelled as a (red), b (green) and c (blue), respectively. [Symmetry code: (ii) 1/2 - x, -1/2 + y, 1/2 - z; (iii) 1/2 + x, 3/2 - y, 1/2 + z; (iv) -x + 1, -y + 1, -z + 1.]
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2961017&req=5

Fap2: Molecular packing of racemic uridine units. The dimeric units of opposite chirality, (2'R*,6R'*,8'R*)- and (2'S*,6'S*,8'S*)-uridines are connected to each other by intermolecular hydrogen bonds. Dashed lines represent hydrogen bonds. Most hydrogen atoms that are not involved in hydrogen bonding, have been omitted for clarity. The origin of the unit cell is labelled as O while cell axes are labelled as a (red), b (green) and c (blue), respectively. [Symmetry code: (ii) 1/2 - x, -1/2 + y, 1/2 - z; (iii) 1/2 + x, 3/2 - y, 1/2 + z; (iv) -x + 1, -y + 1, -z + 1.]
Bottom Line: Each of the O atoms in the tetra-hydro-pyran rings adopts an axial position on the neighbouring ring.This bis--diaxial conformation is adopted, thus gaining maximum stablization from the anomeric effect.The silyl-protected hydroxy-methyl and uracil substituents adopt equatorial positions on their associated tetra-hydro-pyran rings, thereby minimizing unfavourable steric inter-actions.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Univerisity of Auckland, Private Bag 92019, Auckland, New Zealand.

ABSTRACT
The crystal structure of the title compound, C(30)H(38)N(2)O(5)Si, has been investigated to establish the relative stereochemistry at the spiro ring junction and the two anomeric centres. Each of the O atoms in the tetra-hydro-pyran rings adopts an axial position on the neighbouring ring. This bis--diaxial conformation is adopted, thus gaining maximum stablization from the anomeric effect. The silyl-protected hydroxy-methyl and uracil substituents adopt equatorial positions on their associated tetra-hydro-pyran rings, thereby minimizing unfavourable steric inter-actions. The dimeric (2'R*,6'R*,8'R*)- and (2'S*,6'S*,8'S*)-uridine units are connected to each other across crystallographic inversion centres via inter-molecular N-H⋯O hydrogen bonds.

No MeSH data available.


Related in: MedlinePlus