Kathrine V. Booth

6-De­oxy-α-l-talopyran­ose

X-ray crystallography showed that the title compound, C6H12O5, crystallizes in the α-pyranose form with the six-membered ring in a chair conformation. The crystal structure exists as a three-dimensional hydrogen-bonded network of molecules with each molecule acting as a donor and aceptor for four hydrogen bonds. The absolute configuration was determined by the use of l-fucose as starting material.

1-De­oxy-d-galactitol (l-fucitol)

1-Deoxy-d-galactitol, C6H14O5, exists in the crystalline form as hydrogen-bonded layers of molecules running parallel to the ac plane, with each molecule acting as a donor and acceptor of five hydrogen bonds.

2‐Azido‐2‐de­oxy‐2,4‐C‐dimethyl‐3,4‐O‐isopropyl­idene‐l‐ribono‐1,5‐lactone

The relative configuration of the title lactone, C10H15N3O4, a compound of value in the synthesis of complex pyrrolidines, was determined by X-ray crystallographic analysis.

1-De­oxy-l-mannitol (6-de­oxy-l-mannitol or l-rhamnitol)

The crystalline form of 1-deoxy-l-mannitol, C6H14O5, exists as an extensively hydrogen-bonded structure with each molecule acting as a donor and acceptor for five hydrogen bonds. There are no unusual crystal-packing features; the absolute configuration was determined from the use of 6-deoxy-l-mannose (l-rhamnose) as the starting material.

2,6-Dide-oxy-2,6-imino-l-glycero-d-ido-heptitol.

The title molecule, C7H15NO5, the major product from selective enzymatic oxidation followed by hydrogenolysis of the corresponding azidoheptitol, was found by X-ray crystallography to exisit in a chair conformation with three axial hydroxyl groups. One of the hydroxymethyl groups is disordered over two sets of sites in a 0.590 (3):0.410 (3) ratio. In the crystal, O—H⋯O, O—H⋯(O,O), O—H⋯N and N—H⋯O hydrogen bonding occurs.

2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-lyxono-1,4-lactone

X-ray crystallography unequivocally showed that protection of the free hydroxyl group of 3,5-O-benzylidene-d-lyxono-1,4-lactone with diphenyldiazomethane proceeded with retention of configuration to give the title compound, C25H22O5. The crystal structure consists of layers of interlocked molecules lying parallel to the a axis.

tert-Butyl 2-de-oxy-4,5-O-isopropyl-idene-d-gluconate.

The relative configuration of tert-butyl 2-deoxy-4,5-O-isopropylidene-d-gluconate, C13H24O6, an intermediate in the synthesis of 2-deoxy sugars, was determined by X-ray crystallography, and the crystal structure consists of chains of O—H⋯O hydrogen-bonded molecules running parallel to the a axis. There are two molecules in the asymmetric unit. The absolute configuration was inferred from the use of d-erythronolactone as the starting material.

2-De­oxy-2,3-O-isopropyl­idene-2,4-di-C-methyl-β-l-arabinose

X-ray crystallography unequivocally confirmed the stereochemistry of the C atom at position 2 in the carbon scaffold of the title molecule, C10H18O4. The pyranose ring exists in a chair conformation with the methyl group on the C atom in the 2 position in an equatorial configuration. The absolute stereochemistry was determined from the starting material. The crystal structure consists of O—H⋯O hydrogen-bonded chains of molecules running parallel to the b axis.

2,3-O-(S)-Benzyl-idene-2-C-methyl-d-ribono-1,4-lactone.

The crystal structure of the title compound, C13H14O5, establishes (i) the (S) – rather than (R) – configuration at the acetal carbon and (ii) that both the acetal and the lactone form five- rather than six-membered rings; the absolute configuration is determined by the use of 2-C-methyl-d-ribono-1,4-lactone as the starting material. The compound consists of hydrogen-bonded chains of molecules running along the a axis; there are no unusual packing features. Only classical hydrogen bonding has been considered.

2,3-O-Isopropyl­idene-l-apiono-1,4-lactone [(3S,4S)-3,4-dihydr­oxy-4-(hydroxy­methyl)-3,4-di-O-isopropyl­idene-4,5-dihydro­furan-2(3H)-one]

The relative configuration of the title compound, C8H12O5, was unequivocally established by X-ray crystallographic analysis; the absolute configuration was determined by the use of d-ribose as a starting material.