D-Threose

Title: D-Threose
CAS Registry Number: 95-43-2
CAS Name: (2S,3R)-2,3,4-Trihydroxybutanal
Molecular Formula: C4H8O4
Molecular Weight: 120.10
Percent Composition: C 40.00%, H 6.71%, O 53.29%
Literature References: From calcium D-xylonate by oxidation with H2O2: Ruff, Ber. 34, 1370 (1901). Improved procedure using strontium D-xylonate and ferric acetate catalyst: Hockett, J. Am. Chem. Soc. 57, 2260, 2265 (1935). From tetraacetyl-D-xylononitrile: Maquenne, Compt. Rend. 130, 1403 (1900); Ann. Chim. [7] 24, 404 (1901); Bonner, Roth, J. Am. Chem. Soc. 81, 5454 (1959); from monobenzylidene-D-arabitol: Steiger, Reichstein, Helv. Chim. Acta 19, 1016 (1939); from 1,1-diethylsulfonyl-D-threo-3,4,5-trihydroxypent-1-ene: Hough, Taylor, J. Chem. Soc. 1955, 1212; from D-galactose: Perlin, Brice, Can. J. Chem. 34, 541 (1956). Synthesis of DL-threose: Lake, Glattfeld, J. Am. Chem. Soc. 66, 1091 (1944); Schmid, Grob, Helv. Chim. Acta 32, 77 (1949); Sonogashira, Nakagawa, Bull. Chem. Soc. Jpn. 45, 2616 (1972).
Properties: Syrup. Shows mutarotation. Final [a]D20 -12.3° (20 min, c = 4). Very sol in water; slightly in alcohol. Practically insol in ether, petr ether.
Optical Rotation: [a]D20 -12.3° (20 min, c = 4)
Derivative Type: Phenylosazone
Molecular Formula: C16H18N4O2
Molecular Weight: 298.34
Percent Composition: C 64.41%, H 6.08%, N 18.78%, O 10.73%
Properties: Dec 164-165°. Identical with D-erythrose phenylosazone.
Derivative Type: Triacetate
Molecular Formula: C10H14O7
Molecular Weight: 246.21
Percent Composition: C 48.78%, H 5.73%, O 45.49%
Properties: Prisms from abs ethanol, mp 117-118°. [a]D25 +34.4° (c = 2 in chloroform). Soluble in hot water, chloroform, acetone, ethyl acetate; sparingly sol in abs alcohol, methanol, ether.
Melting point: mp 117-118°
Optical Rotation: [a]D25 +34.4° (c = 2 in chloroform)
Dulcin Duloxetine DuPHOS Durapatite Durene

Threose[1]
D-threose.svg
D-Threose
L-threose.svg
L-Threose
Identifiers
CAS number 95-43-2 (D) N, 95-44-3 (L) YesY
PubChem 439665 (D)
ChemSpider 388736 YesY
ChEBI CHEBI:28587 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H8O4
Molar mass 120.10 g mol−1
Appearance Syrup
Solubility in water Very soluble
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Threose is a four-carbon monosaccharide or carbohydrate with molecular formula C4H8O4. It has a terminal aldehyde group rather than a ketone in its linear chain, and so is considered part of the aldose family of monosaccharides. The threose name can be used to refer to both the D- and L-stereoisomers, and more generally to the racemic mixture (D/L-, equal parts D- and L-) as well as to the more generic threose structure (absolute stereochemistry unspecified).

The prefix "threo" which derives from threose (and "erythro" from a corresponding diastereomer erythrose) offer a useful way to describe general organic structures with adjacent chiral centers, where "the prefixes... designate the relative configuration of the centers".[2] As is depicted in a Fischer projection of D-threose, the adjacent substituents will have a syn orientation in the isomer referred to as "threo", and are anti in the isomer referred to as "erythro".[3]

Fischer projections depicting of the two enantiomers of threose