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6-De-oxy-?-l-talopyran-ose.

ABSTRACT: X-ray crystallography showed that the title compound, C(6)H(12)O(5), crystallizes in the ?-pyran-ose form with the six-membered ring in a chair conformation. The crystal structure exists as a three-dimensional hydrogen-bonded network of mol-ecules with each mol-ecule acting as a donor and aceptor for four hydrogen bonds. The absolute configuration was determined by the use of l-fucose as starting material.

SUBMITTER: Booth KV

PROVIDER: S-EPMC2962018 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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6-De-oxy-α-l-talopyran-ose.

Booth K Victoria KV Jenkinson Sarah F SF Fleet George W J GW Gullapalli Pushpakiran P Yoshihara Akihide A Izumori Ken K Watkin David J DJ

Acta crystallographica. Section E, Structure reports online 20080705 Pt 8

X-ray crystallography showed that the title compound, C(6)H(12)O(5), crystallizes in the α-pyran-ose form with the six-membered ring in a chair conformation. The crystal structure exists as a three-dimensional hydrogen-bonded network of mol-ecules with each mol-ecule acting as a donor and aceptor for four hydrogen bonds. The absolute configuration was determined by the use of l-fucose as starting material. ...[more]

PMID: 21203105

Similar Datasets

Crystal structure of 6-de-oxy-α-l-psico-furan-ose.

Project description:The title compound, C6H12O5, was crystallized from an aqueous solution of 6-de-oxy-l-psicose (6-de-oxy-l-allulose, (3S,4S,5S)-1,3,4,5-tetra-hydroxy-hexan-2-one), and the mol-ecule was confirmed as α-furan-ose with a (3) T 4 (or E 4) conformation, which is a predominant tautomer in solution. This five-membered furan-ose ring structure is the second example in the field of the 6-de-oxy-ketohexose family. The cell volume of the title compound [742.67 (7) Å(3), Z = 4 at room temperature] is only 1.4% smaller than that of β-d-psico-pyran-ose, C6H12O6 (753.056 Å(3), Z = 4 at room temperature).

| S-EPMC4719940 | biostudies-literature

2-De-oxy-?-d-arabino-hexopyran-ose.

Project description:The title compound, C(6)H(12)O(5), is the ?-pyran-ose form of the reducing aldose 2-de-oxy-d-arabino-hexose. The six-membered pyran-ose ring adopts a (4)C(1) conformation, with the anomeric hy-droxy group in axial and the other substituents in equatorial positions. In the crystal, each of the four hy-droxy groups acts as an inter-molecular hydrogen-bond donor function, resulting in a three-dimensional hydrogen-bonded network.

| S-EPMC3201514 | biostudies-literature

1,2,3-Tri-O-acetyl-5-de-oxy-d-ribofuran-ose.

Project description:The title compound, C(11)H(16)O(7), was obtained from the breakage reaction of the glycosidic bond of 5'-de-oxy-2',3'-diacetyl-inosine. The ribofuran-ose ring has a C2-exo, C3-endo twist configuration. No alteration of the relative configuration compared with d-(-)-ribose is observed.

| S-EPMC3011534 | biostudies-literature

2-Acetyl-amino-1,3,4,6-tetra-O-(tri-methyl-silyl)-2-de-oxy-α-d-gluco-pyran-ose.

Project description:The title compound, C20H47NO6Si4, was synthesized by per-O-tri-methyl-silylation of N-acetyl-d-glucosa-mine using chloro-tri-methyl-silane in the presence of hexa-methyl-disiloxane. The tri-methyl-silyl group and acetamido group are located on the same side of the pyran ring, showing an α-configuration glycoside. One of the tri-methyl-silyl groups is disordered over two orientations, with site-occupancy factors of 0.625 (9) and 0.375 (9). In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains along the a-axis direction.

| S-EPMC3685068 | biostudies-literature

Crystal structure of 6-azido-6-de-oxy-1,2-<i>O</i>-iso-propyl-idene-α-d-gluco-furan-ose.

Project description:Short syntheses to high Fsp 3 index natural-product analogues such as imino-sugars are of paramount importance in the investigation of their biological activities and reducing the use of protecting groups is an advantageous synthetic strategy. An iso-propyl-idene group was employed towards the synthesis of seven-membered ring imino-sugars and the title compound, C9H15N3O5, was crystallized as an inter-mediate, in which the THF ring is twisted and the dioxolane ring adopts an envelope conformation: the dihedral angle between the rings is 67.50 (13)°. In the crystal, the hydroxyl groups participate in O-H⋯(O,O) and O-H⋯N hydrogen-bonding inter-actions, which generate chains of mol-ecules propagating parallel to the a-axis direction. There is a notable non-classical C-H⋯O hydrogen bond, which cross-links the [100] chains into (001) sheets.

| S-EPMC7534240 | biostudies-literature

Crystal structure of 3-de-oxy-3-nitro-methyl-1,2;5,6-di-O-iso-propyl-idene-α-d-allo-furan-ose.

Project description:The title compound, C13H21NO7 {systematic name: (3aR,5S,6R,6aR)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-(nitro-meth-yl)tetra-hydro-furo[2,3-d][1,3]dioxole}, consists of a substituted 2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxolane skeleton. The furan-ose ring A adopts a (o)T 4 conformation. The fused dioxolane ring B and the substituent dioxolane ring C also have twisted conformations. There are no strong hydrogen bonds in the crystal structure: only weak C-H⋯O contacts are present, which link the mol-ecules to form a three-dimensional structure.

| S-EPMC4778814 | biostudies-literature

β-d-Galacto-pyranosyl-(1→4)-2-amino-2-de-oxy-α-d-gluco-pyran-ose hydro-chloride monohydrate (lactosamine).

Project description:The title compound, C12H24NO10 +·Cl-·H2O, (I), crystallizes in the monoclinic space group P21 and exists as a monohydrate of a monosubstituted ammonium chloride salt, with the reducing carbohydrate portion existing exclusively as the α-pyran-ose tautomer. The glycosidic bond geometry in (I) is stabilized by an intra-molecular hydrogen bond and is close to that found in crystalline α-lactose. All heteroatoms except gluco-pyran-ose ring O4 participate in an extensive hydrogen-bonding network, which propagates in all directions in the crystal structure of (I).

| S-EPMC9028551 | biostudies-literature

1-Dibenzylamino-1-de-oxy-4,5-O-isopropyl-idene-β-d-fructopyran-ose.

Project description:The title compound C(23)H(29)NO(5), synthesized by the Amadori rearrangement of α-d-glucose with dibenzyl-amine and the ketalization, is shown to be a β-anomer. The fructopyran-ose ring adopts a chair conformation. The two benzene rings form a dihedral angle of 68.9 (1)°. In the crystal, non-classical inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

| S-EPMC3051515 | biostudies-literature

Crystal structure of 3-C-(N-benzyl-oxy-carbon-yl)amino-methyl-3-de-oxy-1,2:5,6-di-O-iso-propyl-idene-α-d-allo-furan-ose.

Project description:The title compound, C21H29NO7 (1) [systematic name: benzyl ({(3aR,5S,6R,6aR)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-di-methyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}meth-yl)carbamate], consists of a substituted 2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxolane skeleton. The furan-ose ring adopts an envelope conformation close to C 3-exo, where the C atom substituted by the benzyl carbamate group is the flap. The fused dioxolane ring also adopts an envelope conformation, as does the terminal dioxolane ring, with in each case an O atom as the flap. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming chains propagating along the b-axis direction.

| S-EPMC4647424 | biostudies-literature

3-De-oxy-1,2-di-O-isopropyl-idene-5-O-tosyl-d-threo-pentofuran-ose.

Project description:In the crystal structure of the title compound, C(15)H(20)O(6)S, the two independent mol-ecules crystalllize in a chiral setting with two different conformations, twisted (4)T(3) and envelope (4)E, for the furan-ose rings. Weak C-H?O contacts strengthen the crystal structure.

| S-EPMC3344058 | biostudies-literature

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