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1,2:5,6-Di-O-iso-propyl-idene-3-C-methyl-?-d-allo-furan-ose.

ABSTRACT: The title carbohydrate, C13H22O6, is a derivative of d-glycose, in which the furan-osidic and iso-propyl-idene rings are in twisted conformations. The mean plane of the furan-osidic ring makes a dihedral angle of 70.32?(18)° with the mean plane of the fused iso-propyl-idene ring. The methyl groups in the other iso-propyl-idene ring are disordered over two sets of sites, with an occupancy ratio of 0.74?(6):0.26?(6). In the crystal, mol-ecules are linked by O-H?O hydrogen bonds into chains with graph-set notation C(5) along [100]. Weak C-H?O interactions also occur.

SUBMITTER: Forezi Lda S

PROVIDER: S-EPMC3790382 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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1,2:5,6-Di-O-iso-propyl-idene-3-C-methyl-α-d-allo-furan-ose.

Forezi Luana da Silva Magalhães Lda S Silva Marcos Moitrel Pequeno MM Santos Fernanda da Costa Fda C Ferreira Vitor Francisco VF de Souza Maria Cecília Bastos Vieira MC

Acta crystallographica. Section E, Structure reports online 20130907 Pt 10

The title carbohydrate, C13H22O6, is a derivative of d-glycose, in which the furan-osidic and iso-propyl-idene rings are in twisted conformations. The mean plane of the furan-osidic ring makes a dihedral angle of 70.32 (18)° with the mean plane of the fused iso-propyl-idene ring. The methyl groups in the other iso-propyl-idene ring are disordered over two sets of sites, with an occupancy ratio of 0.74 (6):0.26 (6). In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds into chains with gr ...[more]

PMID: 24098204

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Crystal structure of 3-C-(N-benzyl-oxy-carbon-yl)amino-methyl-3-de-oxy-1,2:5,6-di-O-iso-propyl-idene-?-d-allo-furan-ose.

Project description:The title compound, C21H29NO7 (1) [systematic name: benzyl ({(3aR,5S,6R,6aR)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-di-methyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}meth-yl)carbamate], consists of a substituted 2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxolane skeleton. The furan-ose ring adopts an envelope conformation close to C 3-exo, where the C atom substituted by the benzyl carbamate group is the flap. The fused dioxolane ring also adopts an envelope conformation, as does the terminal dioxolane ring, with in each case an O atom as the flap. In the crystal, mol-ecules are linked by N-H?O and C-H?O hydrogen bonds, forming chains propagating along the b-axis direction.

| S-EPMC4647424 | biostudies-literature

Crystal structure of 3-de-oxy-3-nitro-methyl-1,2;5,6-di-O-iso-propyl-idene-?-d-allo-furan-ose.

Project description:The title compound, C13H21NO7 {systematic name: (3aR,5S,6R,6aR)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-(nitro-meth-yl)tetra-hydro-furo[2,3-d][1,3]dioxole}, consists of a substituted 2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxolane skeleton. The furan-ose ring A adopts a (o)T 4 conformation. The fused dioxolane ring B and the substituent dioxolane ring C also have twisted conformations. There are no strong hydrogen bonds in the crystal structure: only weak C-H?O contacts are present, which link the mol-ecules to form a three-dimensional structure.

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1,2:1',2'-Di-O-iso-propyl-idenedi-furan-ose-C12 higher carbon sugar.

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3,6-Didehydro-5-hy-droxy-1,2-O-iso-propyl-idene-5-C-nitro-meth-yl-?-d-gluco-furan-ose.

Project description:The title compound, C(10)H(15)NO(7), consists of one methyl-enedi-oxy ring and two fused tetra-hydro-furan rings. The three fused rings exhibit cis arrangements at the ring junctions. One O atom of a tetra-hydro-furan ring and the H atoms bound to the neighboring C atoms are disordered over two orientations with site-occupancy factors of 0.69?(1) and 0.31?(1). intra-molecular O-H?O and C-H?O inter-actions stabilize the mol-ecular conformation. In the crystal structure, inter-molecular O-H?O and C-H?O inter-actions link the mol-ecules into a three-dimensional network.

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Crystal structure of 6-azido-6-de-oxy-1,2-<i>O</i>-iso-propyl-idene-α-d-gluco-furan-ose.

Project description:Short syntheses to high Fsp 3 index natural-product analogues such as imino-sugars are of paramount importance in the investigation of their biological activities and reducing the use of protecting groups is an advantageous synthetic strategy. An iso-propyl-idene group was employed towards the synthesis of seven-membered ring imino-sugars and the title compound, C9H15N3O5, was crystallized as an inter-mediate, in which the THF ring is twisted and the dioxolane ring adopts an envelope conformation: the dihedral angle between the rings is 67.50 (13)°. In the crystal, the hydroxyl groups participate in O-H⋯(O,O) and O-H⋯N hydrogen-bonding inter-actions, which generate chains of mol-ecules propagating parallel to the a-axis direction. There is a notable non-classical C-H⋯O hydrogen bond, which cross-links the [100] chains into (001) sheets.

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Crystal structure of 3-O-benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-yl)-1,2-O-iso-propyl-idene-?-d-erythro-furan-ose.

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The crystal structures of 3-O-benzyl-1,2-O-iso-propyl-idene-5-O-methane-sulfonyl-6-O-tri-phenyl-methyl-?-d-gluco-furan-ose and its azide displacement product.

Project description:The effect of different leaving groups on the substitution versus elimination outcomes with C-5 d-glucose derivatives was investigated. The stereochemical configurations of 3-O-benzyl-1,2-O-iso-propyl-idene-5-O-methane-sulfonyl-6-O-tri-phenyl-methyl-?-d-gluco-furan-ose, C36H38O8S (3) [systematic name: 1-[(3aR,5R,6S,6aR)-6-benz-yloxy-2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(trit-yloxy)ethyl methane-sulfonate], a stable inter-mediate, and 5-azido-3-O-benzyl-5-de-oxy-1,2-O-iso-propyl-idene-6-O-tri-phenyl-methyl-?-l-ido-furan-ose, C35H35N3O5 (4) [systematic name: (3aR,5S,6S,6aR)-5-[1-azido-2-(trit-yloxy)eth-yl]-6-benz-yloxy-2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxole], a substitution product, were examined and the inversion of configuration for the azido group on C-5 in 4 was confirmed. The absolute structures of the mol-ecules in the crystals of both compounds were confirmed by resonant scattering. In the crystal of 3, neighbouring mol-ecules are linked by C-H?O hydrogen bonds, forming chains along the b-axis direction. The chains are linked by C-H?? inter-actions, forming layers parallel to the ab plane. In the crystal of 4, mol-ecules are also linked by C-H?O hydrogen bonds, forming this time helices along the a-axis direction. The helices are linked by a number of C-H?? inter-actions, forming a supra-molecular framework.

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(R)-3,4,5-Tride-oxy-5,6-didehydro-1,2-O-(2,2,2-trichloro-ethyl-idene)-?-d-gluco-furan-ose-6,3-carbolactone: a new derivative of ?-chloralose.

Project description:THE TITLE COMPOUND [SYSTEMATIC NAME: (R)-2-trichloro-methyl-3a,3b,7a,8a-tetra-hydro-5H-pyrano[2',3':4,5]furano[2,3-d][1,3]dioxol-5-one], C(9)H(7)Cl(3)O(5), a triyclic system that contains a central ?-d-furan-ose ring cis-fused with a dioxolane ring as well as a ?-lactone ring, exhibits a twisted conformation. The CCl(3) group has an axial orientation. The furan-ose ring approximates an envelope conformation due to the ?,?-unsaturated lactone functionality. The asymmetric unit contains two independent mol-ecules with almost identical geometries.

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Crystal structure of 1,2,3,5-di-O-methyl-ene-?-d-xylo-furan-ose.

Project description:The title compound, C7H10O5, was synthesized by reaction of d-xylose with paraformaldehyde. In the crystal, the central part of the mol-ecule consists of a five-membered C4O ring with an envelope conformation, with the methine C atom adjacent to the O atom being the flap. The protected O atoms of both cyclic acetal groups are oriented so that the four chiral C atoms of the furan-ose part show an R configuration. C-H?O hydrogen bonds are present between adjacent mol-ecules, generating a three-dimensional network.

| S-EPMC4645044 | biostudies-literature

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