Browse
Submit Data
Databases
API
Help

Dataset Information

17 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano-yl}-1,3-oxazolidin-2-one.

ABSTRACT: The title compound, C(19)H(24)ClNO(5), was synthesized and subsequently employed in an Evans alkyl-ation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (-)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an anti-periplanar arrangement to minimize van der Waals repulsions. Furthermore, the Cl atom and the acetonide-protected secondary alcohol are also in an anti-periplanar arrangement with a torsion angle of 173.64?(14)°. The absolute configuration was determined and agrees with the configuration of the used chiral auxiliary.

SUBMITTER: Bording S

PROVIDER: S-EPMC3254509 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano-yl}-1,3-oxazolidin-2-one.

Börding Sandra S Strohmann Carsten C Preut Hans H Hiersemann Martin M

Acta crystallographica. Section E, Structure reports online 20111217 Pt 1

The title compound, C(19)H(24)ClNO(5), was synthesized and subsequently employed in an Evans alkyl-ation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (-)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an anti-periplanar arrangement to minimize van der Waals repulsions. Furthermore, the Cl atom and the acetonide-protected s ...[more]

PMID: 22259453

Similar Datasets

(4S)-4-Benzyl-N-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]sulfon-yl}-2-oxo-1,3-oxazolidine-3-carboxamide.

Project description:The title compound, C(21)H(21)N(3)O(7)S, contains an oxazolidinone ring and a sulfonamide group, both characteristic for biologically and pharrmaceutically active compounds. Both stereogenic centres reveal an S absolute configuration. The two oxazolidinone rings are in an envelope conformation with the methyl-ene carbon flap atoms deviating by 0.428?(1) and 0.364?(2)?Å from the best least-square planes formed by the four other ring atoms. An intra-molecular N-H?O hydrogen bond contributes to the folded conformation of the mol-ecule. In the crystal, weak inter-molecular C-H?O inter-actions connect the mol-ecules into helices along the the twofold screw axes.

| S-EPMC3007004 | biostudies-literature

(S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid.

Project description:The Kiliani reaction on 1-de-oxy-(N,N-dimethyl-amino)-d-fructose, itself readily available from reaction of dimethyl-amine and d-glucose, proceeded to give access to the title ?-sugar amino acid, C(15)H(27)NO(7). X-ray crystallography determined the stereochemistry at the newly formed chiral center. There are two mol-ecules in the asymmetric unit; they are related by a pseudo-twofold rotation axis and have very similar geometries, differing only in the conformation of one of the acetonide rings. All the acetonide rings adopt envelope conformations; the flap atom is oxygen in three of the rings, but carbon in one of them. There are two strong hydrogen bonds between the two independent mol-ecules, and further weak hydrogen bonds link the mol-ecules to form infinite chains running parallel to the a axis.

| S-EPMC2915345 | biostudies-literature

(4S)-4-[(R)-Chloro-(4-nitro-phen-yl)meth-yl]-1,3-oxazolidin-2-one.

Project description:In the title compound, C10H9ClN2O4, the oxazolidinone ring adopts a near-planar conformation, with mean and maximum deviations of 0.0204?(8) and 0.0328?(8)?Å, respectively. The nitro group is twisted slightly from the plane of the benzene ring, making a dihedral angle of 6.79?(3)°. The dihedral angle between the mean oxazolidinone plane and the benzene ring is 56.21?(3)°. In the crystal, N-H?O hydrogen bonds and N-O?? inter-actions [O?centroid distances = 3.478?(1) and 3.238?(1)?Å] dominate the packing, forming infinite zigzag chains along the b-axis direction. Neighbouring chains are linked together through C-H?O and C-H?Cl inter-actions. The absolute configuration of the two stereogenic centres was determined using the anomalous dispersion of the Cl atom.

| S-EPMC3648307 | biostudies-literature

(2S,4S)-3-Benzoyl-4-benzyl-2-tert-but-yl-1,3-oxazolidin-5-one.

Project description:In the title compound, C(21)H(23)NO(3), the central oxazolidinone ring is approximately planar, the maximum deviation from the plane through the central ring being 0.043?(1)?Å. The tert-butyl and benzyl substituents are cis to each other and trans to the N-benzoyl group. The inter-planar angle between the aromatic rings of the C-benzyl and N-benzoyl groups is 81.10?(4)°.

| S-EPMC3435759 | biostudies-literature

(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-carboxy-propanoate.

Project description:In the title compound, C(10)H(16)O(6), the five-membered ring has an envelope conformation. The packing involves hydrogen-bonded carboxylic acid inversion dimers and three C-H?O inter-actions.

| S-EPMC2969742 | biostudies-literature

(4S)-(-)-4-Benzyl-2,2-dimethyl-3-o-toluoyl-1,3-oxazolidine.

Project description:The absolute configuration of the title compound, C(20)H(23)NO(2), has been confirmed as 4S. The benzyl residue and H atom at the asymmetric C-atom centre occupy pseudo-axial and bis-ectional positions, respectively. The oxazolidine ring adopts an envelope conformation. In the crystal structure, the mol-ecular packing is stabilized by non-classical C-H?O hydrogen bonds.

| S-EPMC3009175 | biostudies-literature

(R)-2-[(R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-1,3-oxathio-lan-5-one.

Project description:In the title compound, C(8)H(12)O(4)S, the two five-membered rings both adopt envelope conformations. In the crystal, weak C-H?O inter-actions link neighbouring mol-ecules.

| S-EPMC2969249 | biostudies-literature

(4-Benzyl-2-oxo-1,3-oxazolidin-5-yl)methyl methane-sulfonate.

Project description:The title compound, C(12)H(15)NO(5)S, features an approximately planar five-membered oxazolidin ring (r.m.s. deviation = 0.045 Å) with the peripheral benzyl and methyl methane-sulfonate residues lying to either side of the plane. In the crystal, N-H⋯O hydrogen bonds, involving one of the sulfur-bound oxo groups as acceptor, lead to the formation of supra-molecular chains along the b axis. These chains are reinforced by C-H⋯O contacts with the carbonyl O atom accepting three such inter-actions. The structure was refined as a racemic twin, with the major component being present 89% of the time.

| S-EPMC2979937 | biostudies-literature

(4S,5S)-2-(4-Chloro-phen-yl)-1,3-dioxolane-4,5-dicarboxamide.

Project description:The title compound, C(11)H(11)ClN(2)O(4), is an important inter-mediate for the preparation of platinum anti-cancer drugs. The dioxolane ring adopts a twist conformation with an equatorially attached chloro-phenyl substituent. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to (001) by N-H?O and C-H?O hydrogen bonds.

| S-EPMC2977328 | biostudies-literature

(1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethyl-ene-8,20-diaza-dispiro-[5.6.5.6]tetra-cosa-7,19-diene.

Project description:The crystal structure of the title compound, C(34)H(54)N(2)O(4), has been solved in order to prove the relative and absolute chirality of the newly-formed stereocentres which were established using an asymmetric Diels-Alder reaction at an earlier stage in the synthesis. This unprecedented stable dialdimine contains a 14-membered ring and was obtained as the minor diastereoisomer in the Diels-Alder reaction. The absolute stereochemistry of the stereocentres of the acetal functionality was known to be R based on the use of a chiral (R)-tris-ubstituted dienophile derived from enanti-opure (S)-glyceraldehyde. The assignment of the configuration in the dienophile and the title di-aldimine differs from (S)-glyceraldehyde due to a change in the priority order of the substituents. The crystal structure establishes the presence of six stereocentres all attributed to be R. The 14-membered ring contains two aldimine bonds [C-N = 1.258 (2) and 1.259 (2) Å]. It adopts a similar conformation to that proposed for trans-trans-cyclo-tetra-deca-1,8-dienes.

| S-EPMC3006943 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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