Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Betulin 3,28-di-O-tosyl-ate.

ABSTRACT: The title compound, C44H62O6S2 {systematic name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-penta-methyl-1-(prop-1-en-2-yl)-3a-[(tos-yloxy)meth-yl]icosa-hydro-1H-cyclo-penta-[a]chrysen-9-yl 4-methyl-benzene-sulfonate}, was obtained by tosyl-ation of naturally occurring betulin. All the cyclo-hexane rings adopt chair conformations and the cyclo-pentane ring adopts a twisted envelope conformation, with the C atom bearing the tosyl-methyl substituent forming the flap. In the crystal, mol-ecules form a three-dimensional network through multiple weak C-H?O hydrogen bonds.

SUBMITTER: Peipins U

PROVIDER: S-EPMC4158509 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Betulin 3,28-di-O-tosyl-ate.

Peipiņš Uldis U Freimanis Niks N Stepanovs Dmitrijs D Mishnev Anatoly A Turks Māris M

Acta crystallographica. Section E, Structure reports online 20140723 Pt 8

The title compound, C44H62O6S2 {systematic name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-penta-methyl-1-(prop-1-en-2-yl)-3a-[(tos-yloxy)meth-yl]icosa-hydro-1H-cyclo-penta-[a]chrysen-9-yl 4-methyl-benzene-sulfonate}, was obtained by tosyl-ation of naturally occurring betulin. All the cyclo-hexane rings adopt chair conformations and the cyclo-pentane ring adopts a twisted envelope conformation, with the C atom bearing the tosyl-methyl substituent forming the flap. In the crystal, ...[more]

PMID: 25249923

Similar Datasets

(Phenyl-iodos-yl)benzene tosyl-ate dihydrate.

Project description:The structure of the title salt (systematic name: oxodiphenyl-λ5-iodanylium 4-methyl-benzene-sulfonate dihydrate), C12H10IO+·C7H7O3S-·2H2O, at 150 K, has monoclinic (P21/c) symmetry. The mol-ecular structure features an angular (phenyl-iodos-yl)benzene cation, the geometry of which was hitherto undescribed in the literature: in the cation, both I-C bonds are approximately normal to the I=O bond, forming a C-I-C angle of 95.36 (4)°. The crystal structure displays O-H⋯O, O-H⋯I and O-H⋯S hydrogen bonding.

| S-EPMC9462033 | biostudies-literature

4-(4-Bromo-styr-yl)-1-methylpyridinium tosyl-ate.

Project description:In the cation of the title compound, C14H13BrN(+)·C7H7O3S(-), the dihedral angle between the benzene and pyridine rings is 8.34?(11)°. The Br atom is disordered over two positions with site occupancies of 0.74?(2) and 0.26?(2). The mol-ecular structure is stabilized by a weak intra-molecular C-H?O inter-actions. The crystal structure exhibits weak C-H?O and ?-? [centroid-centroid distance = 3.7466?(17)?Å] inter-actions, forming a three dimensional network.

| S-EPMC3648231 | biostudies-literature

(25R)-6?-Hy-droxy-5?-spiro-stan-3?-yl tosyl-ate.

Project description:The title steroid, C34H50O6S, is an inter-mediate on the synthetic route between diosgenin and brassinosteroids, which possess the A ring modified with the 2?,3?-diol functionality. The polycyclic spiro-stan system has the expected conformation, with six-membered rings adopting chair forms and the five-membered rings envelope forms (flap atoms are the methine C atom in the C/D-ring junction and the spiro C atom connecting rings E and F). The 3?-tosyl-ate group is oriented in such a way that S=O bonds are engaged in inter-molecular hydrogen bonds with O-H and C-H donors. Chains of mol-ecules are formed along [100] via O-H?O hydrogen bonds, and secondary weak C-H?O inter-actions connect two neighbouring chains in the [001] direction.

| S-EPMC3589000 | biostudies-literature

Ethyl 4-hydr-oxy-9-tosyl-9H-carbazole-3-carboxyl-ate.

Project description:In the title compound, C(22)H(19)NO(5)S, the carbazole skeleton is nearly planar [maximum deviation = 0.043?(1)?Å] with the pyrrole ring oriented at dihedral angles of 2.32?(6) and 1.77?(6)° with respect to the adjacent benzene rings. The dihedral angle between the benzene ring of the tosyl group and the carbazole skeleton is 82.25?(5)°. Intra-molecular O-H?O hydrogen bonding results in the formation of a planar six-membered ring, which is oriented at a dihedral angle of 3.06?(4)° with respect to the adjacent carbazole skeleton. In the crystal structure, weak inter-molecular C-H?O inter-actions link the mol-ecules into infinite chains and ?-? contacts between the benzene rings and between the pyrrole and benzene rings [centroid-centroid distances = 3.374?(1) and 3.730?(1)?Å, respectively] may further stabilize the structure. A weak C-H?? inter-action is also present.

| S-EPMC2969395 | biostudies-literature

trans-4-Nitro-phenyl 4-(tosyl-oxymeth-yl)cyclo-hexa-necarboxyl-ate.

Project description:The title compound, C(21)H(23)NO(7)S, is an important inter-mediate in the synthesis of poly(amido-amine) dendrimers. The cyclo-hexane ring adopts a chair conformation. The dihedral angle between the two aromatic rings is 69.5 (2)°. The mol-ecules are linked into a zigzag chain along the b axis by C-H⋯O hydrogen bonds.

| S-EPMC2960325 | biostudies-literature

Dimethyl 2,2'-di-nitro-biphenyl-4,4'-di-carboxyl-ate.

Project description:The title compound, C16H12N2O8, exhibits two near-planar aromatic ester groups with ar-yl-ester dihedral angles of 2.1 (2) and 4.2 (3)°. The dihedral angle between the aromatic rings is 58.0 (1)°. The two nitro groups are tilted slightly from the plane of the aromatic rings, making dihedral angles of 14.1 (1) and 8.2 (2)°. In the crystal, mol-ecules are connected by weak C-H⋯O inter-actions, forming a three-dimensional network.

| S-EPMC3998396 | biostudies-literature

4-(3-Eth-oxy-4-hydroxy-styr-yl)-1-methyl-pyridinium tosyl-ate monohydrate.

Project description:In the title compound, C(16)H(18)NO(2) (+)·C(7)H(7)O(3)S(-)·H(2)O, the dihedral angle between the pyridyl and benzene rings of the pyridinium cation is 0.2 (1)°. The benzene ring of the tosyl-ate anion makes a dihedral angle of 4.8 (2)° with the best mean plane of the pyridinium cation. The pyridinium cation and the tosyl-ate anion are hydrogen bonded to the water mol-ecule, and the crystal packing is further stabilized by inter-molecular C-H⋯O and π-π inter-actions [centroid-centroid separations of 3.648 (3) and 3.594 (2) Å.

| S-EPMC2967981 | biostudies-literature

Dimethyl 3,3'-di-meth-oxy-biphenyl-4,4'-di-carboxyl-ate.

Project description:In the title compound, C18H18O6, the biphenyl moiety is twisted with a dihedral angle of 29.11 (10)°. The carbometh-oxy groups form C-C-C-O torsion angles of -18.3 (3) and -27.7 (3)° with the attached rings, as a result of steric hindrances from the nearby meth-oxy groups. In the absence of stacking inter-actions and with no H⋯O contacts shorter than 2.7 Å, the packing is dominated by weaker van der Waals inter-actions.

| S-EPMC3998533 | biostudies-literature

Dipentyl 2,6-di-amino-benzo[1,2-b:4,5-b']di-furan-3,7-di-carboxyl-ate.

Project description:The title compound, C22H28N2O6, crystallizes with one half-mol-ecule in the independent unit, the mol-ecule being located on an inversion centre. The penthyl groups are in the all-trans conformation and an almost planar conformation of the whole mol-ecule is observed [maximum deviation from the least-squares plane through all non-H atoms is 0.0229?(17)?Å for an N atom]. The amino groups are involved in intra- and inter-molecular hydrogen bonds. Intra-molecular hydrogen bonding involving the amino group and ester carbonyl helps to lock the syn conformation of the ester with respect to the amino group. In the crystal, N-H?O hydrogen bonding involving the amino group and the furan and ester carbonyl O atoms self-assembles the mol-ecules into a two-dimensional hydrogen-bonded network parallel to (010) that displays inter-digital packing sustained by alk-yl-alkyl inter-actions.

| S-EPMC3790396 | biostudies-literature

Dimethyl 2-amino-biphenyl-4,4'-di-carboxyl-ate.

Project description:The title compound, C16H15NO4, exhibits two near-planar aromatic ester groups with a maximum aryl-ester torsion angle of 1.9?(2)°. The dihedral angle between the benzene rings is 44.7?(1)°. In the crystal, N-H?O hydrogen bonding is observed along with C-H?O contacts, forming chanins along [101]. No ?-? inter-actions were noted between the benzene rings.

| S-EPMC3648318 | 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