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)

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