9381. d-Threose

Nomenclature

CAS number: 95-43-2
(2S,3R)-2,3,4-Trihydroxybutanal.
C4H8O4; mol wt 120.10.
C 40.00%, H 6.71%, O 53.29%.

Description and 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).

Chemical structure

Properties

Syrup. Shows mutarotation. Final [α]D20 12.3° (20 min, c = 4). Very sol in water; slightly in alcohol. Practically insol in ether, petr ether.

Derivative

Phenylosazone.
C16H18N4O2; mol wt 298.34.
C 64.41%, H 6.08%, N 18.78%, O 10.73%.

Properties

Dec 164-165°. Identical with d-erythrose phenylosazone.

Derivative

Triacetate.
C10H14O7; mol wt 246.21.
C 48.78%, H 5.73%, O 45.49%.

Properties

Prisms from abs ethanol, mp 117-118°. [α]D25 +34.4° (c = 2 in chloroform). Soluble in hot water, chloroform, acetone, ethyl acetate; sparingly sol in abs alcohol, methanol, ether.