Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

The synthesis of the 2,3-difluorobutan-1,4-diol diastereomers.

ABSTRACT: The diastereoselective synthesis of fluorinated building blocks that contain chiral fluorine substituents is of interest. Here we describe optimisation efforts in the synthesis of anti-2,3-difluorobutane-1,4-diol, as well as the synthesis of the corresponding syn-diastereomer. Both targets were synthesised using an epoxide opening strategy.

SUBMITTER: Szpera R

PROVIDER: S-EPMC5753060 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

The synthesis of the 2,3-difluorobutan-1,4-diol diastereomers.

Szpera Robert R Kovalenko Nadia N Natarajan Kalaiselvi K Paillard Nina N Linclau Bruno B

Beilstein journal of organic chemistry 20171227

The diastereoselective synthesis of fluorinated building blocks that contain chiral fluorine substituents is of interest. Here we describe optimisation efforts in the synthesis of <i>anti</i>-2,3-difluorobutane-1,4-diol, as well as the synthesis of the corresponding <i>syn</i>-diastereomer. Both targets were synthesised using an epoxide opening strategy. ...[more]

PMID: 30018668

Similar Datasets

1,4-Dibromo-naphthalene-2,3-diol.

Project description:In the title compound (r.m.s. deviation for the non-H atoms = 0.020?Å), C(10)H(6)Br(2)O(2), an intra-molecular O-H?O hydrogen bond generates an S(6) ring. In the crystal, the same H atom also forms an inter-molecular O-H?O hydrogen bond, generating a C(2) chain propagating in [100]. The other O-H hydrogen forms a weak O-H?? inter-action, and short Br?Br contacts [3.5972?(9)?Å] also occur.

| S-EPMC3213464 | biostudies-literature

1,4-Dichloro-naphthalene-2,3-diol.

Project description:The achiral planar (maximum deviation 0.014?Å) title compound, C(10)H(6)Cl(2)O(2), crystallizes in the chiral space group P2(1)2(1)2(1) in an arrangement incorporating conventional O-H?O hydrogen bonding leading to a supra-molecular chain.

| S-EPMC2968610 | biostudies-literature

2,3-Dichloro-benzene-1,4-diol.

Project description:The achiral title compound, C(6)H(4)Cl(2)O(2), crystallizes with O-H⋯O hydrogen bonding linking mol-ecules into layers. Between layers there are chains of Cl⋯Cl⋯Cl inter-actions with alternating distances of 3.274 (2) and 3.742 (2) Å. Augmenting this arrangement there are also C-H⋯Cl (2.97 and 3.17 Å) and Cl⋯π (shortest distances 3.40 and 3.54 Å) inter-actions.

| S-EPMC2977781 | biostudies-literature

1,2,3,4-Tetra-hydro-1,4-methano-naphthalene-2,3-diol.

Project description:The title compound, C(11)H(12)O(2), is an inter-mediate in the synthesis of Varenicline, a nicotinic receptor partial agonist used to treat smoking addiction. In the crystal structure, there is an intra-molecular O-H⋯O hydrogen bond that generates an S(5) ring motif. Inter-molecular O-H⋯O hydrogen bonds form centrosymmetric dimers and also link these dimers into chains along the a axis.

| S-EPMC2967988 | biostudies-literature

2,2,3,3-Tetra-fluoro-butane-1,4-diol.

Project description:In the title compound, C(4)H(6)F(4)O(2), a partially fluorinated aliphatic diol, cooperative O-H⋯O hydrogen bonds form R(2) (2)(14) rings, which are connected into infinite layers parallel to the (100) plane by C(7) chains. A C-H⋯F link is also seen.

| S-EPMC2967951 | biostudies-literature

Naphthalene-2,3-diol-imidazole (1/1).

Project description:In the title cocrystal, C(10)H(8)O(2)·C(3)H(4)N(2), inter-molecular O-H?O and N-H?O hydrogen bonds connect the naphthalene-2,3-diol and imidazole mol-ecules into a two-dimensional supra-molecular framework.

| S-EPMC2960591 | biostudies-literature

Synthesis, crystal structures and Hirshfeld surface analysis of 1,4-dibenzyl-6-methyl-1,4-di-hydro-quinoxaline-2,3-dione.

Project description:The title quinoxaline mol-ecule, C23H20N2O2, is not planar, the dihedral angle angle between the mean planes of the benzene rings being 72.54 (15)°. In the crystal, mol-ecules are connected into chains extending parallel to (10) by weak C-H⋯O hydrogen bonds. Weak C-H⋯π inter-actions link the chains, forming a three-dimensional network structure. Hirshfeld surface analysis revealed that the most important contributions for the crystal packing are from H⋯H (48.7%), H⋯C/C⋯H (32.0%), H⋯O/O⋯H (15.4%), C⋯C (1.9%), H⋯N/N⋯H (1.1%) contacts.

| S-EPMC7405587 | biostudies-literature

(E)-1,1,4,4-Tetra-phenyl-but-2-yne-1,4-diol.

Project description:The mol-ecule of the title compound, C(28)H(22)O(2), is centrosymmetric with the inversion centre located at the mid-point of the C C bond [1.178 (5) Å]. The hydroxyl groups therefore lie on either side of the mol-ecule. The crystal structure is stabilized by O-H⋯O hydrogen bonds, leading to the formation of a linear supra-molecular chain along the b axis.

| S-EPMC2983558 | biostudies-literature

1,4-Dibromo-butane-2,3-dione.

Project description:The asymmetric unit of the title compound, C(4)H(4)Br(2)O(2), contains one half-mol-ecule, being located about a centre of inversion. In the crystal, there are no significant inter-molecular inter-actions.

| S-EPMC3515323 | biostudies-literature

Benzene-1,3-diol-1,4-diaza-bicyclo-[2.2.2]octane (1/1).

Project description:There are two independent but virtually identical mol-ecules of each component in the asymmetric unit of the title 1:1 adduct, C(6)H(12)N(2)·C(6)H(6)O(2). In the crystal, the constituents are connected into a supra-molecular chain along the b axis by O-H?N hydrogen bonds. Weak C-H?O bonds cross-link the chains.

| S-EPMC3007329 | 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