Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

(3R,4R,5R)-5-(Acetamido-meth-yl)-N-benzyl-3,4-dihy-droxy-tetra-hydro-furan-3-carboxamide.

ABSTRACT: X-ray crystallographic analysis with Cu K? radiation established the relative configurations of the stereogenic centers in the title compound, C(15)H(20)N(2)O(5), and clarified mechanistic ambiguities in the synthesis. The conformation of the five-membered ring approximates twisted, about a C-O bond. The absolute configuration of this carbon-branched dipeptide isostere was known based on the use of d-ribose as the starting material. Refinement of the Flack parameter gave an ambiguous result but the refined Hooft parameter is in agreement with the assumed (d-ribose) absolute structure. The crystal structure consists of N-H?O and O-H?O hydrogen-bonded bi-layers, with the terminal methyl and phenyl groups forming a hydro-phobic inter-layer inter-face. Some weak C-H?O inter-actions are also present.

SUBMITTER: Simone MI

PROVIDER: S-EPMC3009327 | biostudies-other | 2010

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

(3R,4R,5R)-5-(Acetamido-meth-yl)-N-benzyl-3,4-dihy-droxy-tetra-hydro-furan-3-carboxamide.

Simone Michela I MI Edwards Alison A AA Cowley Andrew R AR Fleet George W J GW Watkin David J DJ

Acta crystallographica. Section E, Structure reports online 20101009 Pt 11

X-ray crystallographic analysis with Cu Kα radiation established the relative configurations of the stereogenic centers in the title compound, C(15)H(20)N(2)O(5), and clarified mechanistic ambiguities in the synthesis. The conformation of the five-membered ring approximates twisted, about a C-O bond. The absolute configuration of this carbon-branched dipeptide isostere was known based on the use of d-ribose as the starting material. Refinement of the Flack parameter gave an ambiguous result but ...[more]

PMID: 21588955

Similar Datasets

4,4'-[(2R*,3R*,4R*,5R*)-3,4-Dimethyl-tetra-hydro-furan-2,5-di-yl]diphenol.

Project description:The title mol-ecule, C(18)H(20)O(3), is a furan-oid lignan extracted from the leaves of Larrea tridentata. The relative absolute configuration for the four chiral centers was established, showing that this compound is 4-epi-larreatricin, which has been previously reported in the literature. The mol-ecule displays noncrystallographic C(2) symmetry, with the methyl and phenol substituents alternating above and below the mean plane of the furan ring. The conformation of this ring is described by the pseudorotation phase angle P = 171.3° and the maximum out-of-plane pucker ?(m) = 37.7°. These parameters indicate that the furan ring adopts the same conformation as the ribose residues in B-DNA. The packing is dominated by inter-molecular O-H?O hydrogen bonds. The phenol hy-droxy groups form chains in the [110] direction and these chains inter-act via O-H?O(furan) contacts.

| S-EPMC3470375 | biostudies-literature

Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate.

Project description:The title compound, C(22)H(25)F(5)N(4)O(9), is a stable penta-fluoro-phenyl ester inter-mediate in the synthesis of novel homo-oligomeric structures containing branched carbon chains. The structure is epimeric to the previously characterized dimeric penta-fluoro-phenyl ester with stereochemistry (3R,4R,5R), which was synthesized using d-ribose as starting material. The crystal structure of the title mol-ecule removes any ambiguities arising from the relative stereochemistries of the six chiral centres. Two hydrogen bonds, bifurcating from the NH group, stabilize the crystal: one intra-molecular and one inter-molecular, both involving O atoms of the meth-oxy groups. The asymmetric unit contains two independent mol-ecules not related by any pseudo-symmetry operators. The major conformational differences are localized, leading to one mol-ecule being extended compared to the other. The collected crystal was twinned (twin ratio is 0.939:0.061), and the azide group is positionally disordered over two positions in one mol-ecule [occupancy ratio 0.511?(18):0.489?(18)].

| S-EPMC3009349 | biostudies-literature

N-(2-Carb-oxy-eth-yl)-2,5-dide-oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb-oxy-eth-yl)-3,4-dihy-droxy-5-hy-droxy-methyl-l-proline].

Project description:The absolute stereochemistry of the title compound, C(9)H(15)NO(7), was determined from the use of d-glucuronolactone as the starting material. The compound crystallizes as the zwitterion. The five-membered ring adopts an envelope conformation with the -CH(2)OH-substituted C atom forming the flap. An intramolecular N-H?O hydrogen-bond occurs. In the crystal, the compound exists as a three-dimensional O-H?O intermolecular hydrogen-bonded network with each mol-ecule acting as a donor and acceptor for four hydrogen bonds.

| S-EPMC3470222 | biostudies-literature

(2S,3R,4R,5R)-3,4-Dihydr-oxy-5-(hydroxy-meth-yl)pyrrolidine-2-carboxylic acid [(2S,3R,4R,5R)-3,4-dihydr-oxy-5-(hydroxy-meth-yl)proline].

Project description:The crystal structure of the title compound, C(6)H(11)NO(5), establishes the relative configuration at the four stereogenic centres; the absolute configuration is determined by the use of d-glucuronolactone as the starting material for the synthesis. Mol-ecules are linked by inter-molecular O-H?O and N-H?O hydrogen bonds into a three-dimensional network, with each mol-ecule acting as a donor and acceptor for five hydrogen bonds.

| S-EPMC2970405 | biostudies-other

(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo-[2,3-d]pyrimidin-7-yl)-5-methyl-tetra-hydro-furan-3,4-diol.

Project description:The mol-ecular structure of the title compound, C11H13IN4O3, shows a ribo-furanos-yl-pyrrolo O-C-N-C torsion angle of 59.1 (3)°, with the central C-N bond length being 1.446 (3) Å. The C-I bond length is 2.072 (2) Å. The amino group is coplanar with the attached aromatic ring [C-N-C-N torsion angle = -178.8 (2)°] and forms an intra-molecular N-H⋯I hydrogen bond. In the crystal, O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into puckered layers parallel to (001). These layers are bound to each other by secondary I⋯O inter-actions [3.2250 (17) Å], forming a three-dimensional framework.

| S-EPMC3884313 | biostudies-literature

[(3R*,4R*,5R*)-2,3-Diphenyl-isoxazolidine-4,5-di-yl]dimethanol.

Project description:In the title compound, C(17)H(19)NO(3), the isoxazolidine ring adopts an envelope conformation with the O atom as the flap. In the crystal, O-H⋯O hydrogen bonds form C(2) (3)(14) R(2) (2)(14) motifs.

| S-EPMC3393325 | biostudies-literature

Anilinium 3,4-dihy-droxy-benzoate.

Project description:The asymmetric unit of the title salt, C(6)H(8)N(+)·C(7)H(5)O(4) (-), contains two anilinium cations and two 3,4-dihy-droxy-benzoate anions. An intra-moleculer O-H?O hydrogen bond occurs in each anion. In the crystal, O-H?O and N-H?O hydrogen bonds link the cations and anions into a three-dimensional array. The structure is further consolidated by weak C-H?O inter-actions.

| S-EPMC3415033 | biostudies-literature

3,4-Dihy-droxy-phenethyl acetate.

Project description:In the title compound, C(10)H(12)O(4), the dihedral angle between the acetate group and the aromatic ring is 20.47?(10)°. In the crystal, mol-ecules are linked by O-H?O hydrogen bonds, forming [001] chains. Weak C-H?O inter-actions consolidate the packing.

| S-EPMC3213451 | biostudies-literature

Isopropyl 3,4-dihy-droxy-benzoate.

Project description:In the crystal structure of the title compound, C(10)H(12)O(4), O-H⋯O hydrogen bonds incorporating R(2) (2)(10) and R(2) (2)(14) motifs link mol-ecules into chains along [1[Formula: see text]0]. An intra-molecular O-H⋯O hydrogen bond is also observed.

| S-EPMC3238893 | biostudies-literature

Crystal structures of fac-tri-carbonyl-chlorido-(6,6'-dihy-droxy-2,2'-bi-pyridine)-rhenium(I) tetra-hydro-furan monosolvate and fac-bromido-tricarbon-yl(6,6'-dihy-droxy-2,2'-bi-pyridine)-manganese(I) tetra-hydro-furan monosolvate.

Project description:The structures of two facially coordinated Group VII metal complexes, fac-[ReCl(C10H8N2O2)(CO)3]·C4H8O (I·THF) and fac-[MnBr(C10H8N2O2)(CO)3]·C4H8O (II·THF), are reported. In both complexes, the metal ion is coordinated by three carbonyl ligands, a halide ligand, and a 6,6'-dihy-droxy-2,2'-bi-pyridine ligand in a distorted octa-hedral geometry. Both complexes co-crystallize with a non-coordinating tetra-hydro-furan (THF) solvent mol-ecule and exhibit inter-molecular but not intra-molecular hydrogen bonding. In both crystal structures, chains of complexes are formed due to inter-molecular hydrogen bonding between a hy-droxy group from the 6,6'-dihy-droxy-2,2'-bi-pyridine ligand and the halide ligand from a neighboring complex. The THF mol-ecule is hydrogen bonded to the remaining hy-droxy group.

| S-EPMC4971873 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data