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(3R,4R,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one.

ABSTRACT: The relative configuration of the title compound, C(11)H(18)O(3), which was synthesized using a catalytic asymmetric Gosteli-Claisen rearrangement, a diastereoselective reduction with K-Selectride and an Evans aldol addition, was corroborated by single-crystal X-ray diffraction analysis. The five-membered ring has an envelope conformation with a dihedral angle of 29.46 (16)° between the coplanar part and the flap (the hydr-oxy-bearing ring C atom). In the crystal, mol-ecules are connected via bifurcated O-H⋯(O,O) hydrogen bonds, generating [010] chains.

SUBMITTER: Gille A

PROVIDER: S-EPMC2971977 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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(3R,4R,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one.

Gille Annika A Schürmann Markus M Preut Hans H Hiersemann Martin M

Acta crystallographica. Section E, Structure reports online 20091128 Pt 12

The relative configuration of the title compound, C(11)H(18)O(3), which was synthesized using a catalytic asymmetric Gosteli-Claisen rearrangement, a diastereoselective reduction with K-Selectride and an Evans aldol addition, was corroborated by single-crystal X-ray diffraction analysis. The five-membered ring has an envelope conformation with a dihedral angle of 29.46 (16)° between the coplanar part and the flap (the hydr-oxy-bearing ring C atom). In the crystal, mol-ecules are connected via bi ...[more]

PMID: 21578968

Similar Datasets

(3S,4S,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one.

Project description:The title compound, C(11)H(18)O(3), was synthesized to prove the relative configuration of the corresponding acyclic C1-C8 stereopentade. Mol-ecules are linked via O-H?O hydrogen bonds, forming a chain along the b axis.

| S-EPMC2960667 | biostudies-literature

(3S,4S,5R)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one.

Project description:The relative configuration of the title compound, C(11)H(18)O(3), was corroborated by single-crystal X-ray diffraction analysis. In the crystal, mol-ecules are linked via a O-H?O hydrogen bond and a chain of mol-ecules is formed along [010].

| S-EPMC2968068 | biostudies-literature

(3R,4S,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]tetra-hydro-furan-2-one.

Project description:The title compound, C(11)H(18)O(3), was synthesized to prove the relative configuration of the corresponding acyclic C1-C8 stereopentade. It crystallizes with two mol-ecules in the asymmetric unit, which show only slight differences. The mol-ecules are linked via O-H⋯O hydrogen bonds, resulting in two crystallographically independent chains of mol-ecules propagating in the a-axis direction. The absolute configuration was known from the synthesis.

| S-EPMC2962143 | 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)].

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2-Amino-9-[(1S,3R,4S)-4-hydr-oxy-3-hydroxy-methyl-2-methyl-enecyclo-pent-yl]-1,9-dihydro-6H-purin-6-one monohydrate.

Project description:In the crystal of the title compound, C(12)H(15)N(5)O(3)·H(2)O, the component species are linked by N-H⋯N, N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, forming a three-dimesnional network.

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[(1S,2S,3R,4R)-3-Hydr-oxy-4,7,7-tri-methyl-bicyclo-[2.2.1]heptan-2-yl]methyl[(E)-3-(trimethyl-silyl)prop-2-enyl]selen-onium bromide.

Project description:The title compound, a seleno-nium bromide, C(17)H(33)OSeSi(+)·Br(-), was obtained from the reaction of enanti-omerically pure 4,7,7-trimethyl-2-methyl-selanylbicyclo-[2.2.1]heptan-3-ol and (3-bromopropen-yl)trimethyl-silane in acetone. Due to the chiral bicyclic substituent, the crystal structure is not centrosymmetric and has no symmetry plane, with four chiral C atoms in the cation. The asymmetric unit contains one seleno-nium cation and one bromide anion. C-H⋯Br and O-H⋯Br hydrogen bonds link the ions, forming a one-dimensional R-helical chain-like supra-molecular structure.

| S-EPMC2961745 | biostudies-literature

5-{(2S,3R,4S,5S,6R)-3,4-Dihydr-oxy-6-hydroxy-meth-yl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydr-oxy-6-methyl-tetra-hydro-pyran-2-yloxy]tetra-hydro-pyran-2-yloxy}--7-hydr-oxy-2-(4-hydroxy-phen-yl)chromen-4-one monohydrate.

Project description:In the title compound, C(27)H(30)O(14)·H(2)O, the hydroxy-phenyl ring makes a dihedral angle of 20.05?(11)° with the chromenone ring system. The crystal structure is stabilized by intra- and inter-molecular O-H?O hydrogen bonds. The absolute configuration was assigned on the basis of an analagous structure.

| S-EPMC2959284 | biostudies-literature

3-(2-Hydr-oxy-5-methyl-anilino)isobenzo-furan-1(3H)-one.

Project description:In the mol-ecule of the title compound, C(15)H(13)NO(3), the phthalide ring system is virtually planar, with a dihedral angle of 1.98 (3)° between the fused five- and six-membered rings. The substituted aromatic ring is oriented at a dihedral angle of 57.50 (3)° with respect to the phthalide ring system. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules, forming a three-dimensional network.

| S-EPMC2961204 | biostudies-literature

(5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methyl-cyclo-hex-yloxy]furan-2(5H)-one.

Project description:The title compound, C(18)H(26)ClNO(3), was obtained via a tandem asymmetric Michael addition-elimination reaction of 3,4-dichloro-5-(S)-(l-menth-yloxy)furan-2(5H)-one and 2,5-di-hydro-1H-pyrrole in the presence of potassium fluoride. In the mol-ecule, the nearly planar dihydro-pyrrole ring [maximum atomic deviation = 0.019?(3)?Å] is oriented at a dihedral angle of 10.73?(8)° to the the nearly planar furan-one ring [maximum atomic deviation = 0.011?(2)?Å]; the cyclo-hexane ring adopts a chair conformation. In the crystal, mol-ecules are linked via weak inter-molecular C-H?O hydrogen bonds, forming supra-molecular chains running along the b axis.

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(5R*)-5-[(2S*,5S*)-1-Meth-oxy-5-phenyl-pyrrolidin-2-yl]-3-methyl-furan-2(5H)-one.

Project description:In the title compound, C16H19NO3, the pyrrolidine ring is in a twist conformation. The dihedral angle between the di-hydro-furan ring [maximum deviation = 0.0016?(11)?Å] and the phenyl ring is 47.22?(8)°. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds, forming helical chains along the b-axis direction. The chains are further linked by C-H?? inter-actions to constitute a three-dimensional architecture.

| S-EPMC4158531 | biostudies-literature

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