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

ABSTRACT: 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.

SUBMITTER: Luginina J

PROVIDER: S-EPMC4778814 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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

Lugiņina Jevgeņija J Rjabovs Vitālijs V Stepanovs Dmitrijs D

Acta crystallographica. Section E, Crystallographic communications 20160210 Pt 3

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 pre ...[more]

PMID: 27006795

Similar Datasets

1,2:5,6-Di-O-iso-propyl-idene-3-C-methyl-?-d-allo-furan-ose.

Project description:The title carbohydrate, C13H22O6, is a derivative of d-glycose, in which the furan-osidic and iso-propyl-idene rings are in twisted conformations. The mean plane of the furan-osidic ring makes a dihedral angle of 70.32?(18)° with the mean plane of the fused iso-propyl-idene ring. The methyl groups in the other iso-propyl-idene ring are disordered over two sets of sites, with an occupancy ratio of 0.74?(6):0.26?(6). In the crystal, mol-ecules are linked by O-H?O hydrogen bonds into chains with graph-set notation C(5) along [100]. Weak C-H?O interactions also occur.

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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

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.

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3,6-Didehydro-5-hy-droxy-1,2-O-iso-propyl-idene-5-C-nitro-meth-yl-?-d-gluco-furan-ose.

Project description:The title compound, C(10)H(15)NO(7), consists of one methyl-enedi-oxy ring and two fused tetra-hydro-furan rings. The three fused rings exhibit cis arrangements at the ring junctions. One O atom of a tetra-hydro-furan ring and the H atoms bound to the neighboring C atoms are disordered over two orientations with site-occupancy factors of 0.69?(1) and 0.31?(1). intra-molecular O-H?O and C-H?O inter-actions stabilize the mol-ecular conformation. In the crystal structure, inter-molecular O-H?O and C-H?O inter-actions link the mol-ecules into a three-dimensional network.

| S-EPMC3151982 | biostudies-literature

1,2:1',2'-Di-O-iso-propyl-idenedi-furan-ose-C12 higher carbon sugar.

Project description:In the title compound, C18H28O8, the five-membered ring with one O atom attached to the ethyl substituent has a twisted conformation about the C-O bond. The adjacent cis-fused ring with two O atoms also has a twisted conformation about one of the C-O bonds. The dihedral angle between these rings (all atoms) is 59.05?(12)°. The five-membered ring linked to the ethynyl susbtituent is twisted about a C-C bond; the cis-fused adjacent ring is twisted about a C-O bond [dihedral angle between the rings (all atoms) = 71.78?(12)°]. Two intra-molecular O-H?O hydrogen bonds occur. In the crystal, mol-ecules are linked by O-H?O hydrogen bonds, generating [001] chains.

| S-EPMC3884459 | biostudies-literature

1-O-Benzyl-2,3-O-iso-propyl-idene-6-O-tosyl-?-l-sorbo-furan-ose.

Project description:IN THE TITLE COMPOUND (SYSTEMATIC NAME: {(3aS,5S,6R,6aS)-3a-[(benz-yloxy)meth-yl]-6-hy-droxy-2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxol-5-yl}methyl 4-methyl-benzene-sulfonate), C23H28O8S, the absolute structure and relative stereochemistry of the four chiral centres have been established by X-ray crystallography, with the absolute configuration inferred from the use of l-sorbose as the starting material. The central furan-ose ring adopts a slightly twisted envelope conformation (with the C atom bearing the methyl-benzene-sulfonate substituent as the flap) from which three substituents depart pseudo-axially (-CH2-O-benzyl, -OH and one acetonide O atom) and two substituents pseudo-equatorially (-CH2-O-tosyl and second acetonide O atom). The dioxalane ring is in a flattened envelope conformation with the fused CH C atom as the flap. In the crystal, mol-ecules pack in columns along [010] linked by O-H?O hydrogen bonds involving the furan-ose hy-droxy group and furan-ose ether O atom.

| S-EPMC3772494 | biostudies-other

Methyl 6-de-oxy-6-iodo-2,3-O-iso-propyl-idene-?-d-manno-pyran-oside.

Project description:In the title compound, C10H17IO5, the six-membered tetra-hydro-pyran ring and the five-membered 1,3-dioxolane ring adopt sofa and envelope conformations, respectively. In the crystal, O-H?O and C-H?O hydrogen bonds link the mol-ecules into layers nearly parallel to the bc plane.

| S-EPMC3884490 | 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

4-Cyclo-propyl-1-(6'-de-oxy-1',2'-O-iso-propyl-idene-?-d-gluco-furanos-yl)-1H-1,2,3-triazole.

Project description:In the title compound, C14H21N3O5, the tetra-hydro-furan ring adopts an envelope conformation with the C atom bearing the substituent as the flap. The penta-furan-ose ring adopts a twisted conformation about the C-C bond fusing the rings. The dihedral angle between these rings (all atoms), which are cis fused, is 72.89?(14)°. The cyclo-propane ring is disordered over two orientations in a 0.576?(5):0.424?(5) ratio; the dihedral angles subtended to the triazole ring are 53.3?(11) and 46.6?(9)°, respectively. In the crystal, the mol-ecules are linked by O-H?N and O-H?O hydrogen bonds, generating (001) sheets. A weak C-H?O inter-action also occurs.

| S-EPMC3884407 | biostudies-literature

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

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