D-Threose, CAS:95-43-2

D-Threose
D-Threose is a four-carbon monosaccharide or carbohydrate with molecular formula C4H8O4. 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”. 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”.Title:?D-Threose
CAS Registry Number:?95-43-2CAS Name:?(2S,3R)-2,3,4-TrihydroxybutanalMolecular Formula:?C4H8O4Molecular Weight:?120.10Percent 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:?PhenylosazoneMolecular Formula:?C16H18N4O2Molecular Weight:?298.34Percent Composition:?C 64.41%, H 6.08%, N 18.78%, O 10.73%Properties:?Dec 164-165?. Identical with?D-erythrose phenylosazone.?Derivative Type:?TriacetateMolecular Formula:?C10H14O7Molecular Weight:?246.21Percent 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)CAS Number95-43-2Product NameD-ThreoseIUPAC Name(2S,3R)-2,3,4-trihydroxybutanalMolecular FormulaC4H8O4Molecular Weight120.1 g/molInChIInChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1InChI KeyYTBSYETUWUMLBZ-QWWZWVQMSA-NSMILESC(C(C(C=O)O)O)OSynonyms(2S,3R)-2,3,4-Trihydroxy-butanal; [S-(R*,S*)]-2,3,4,-Trihydroxy-butanal; D-(-)-Threose;Canonical SMILESC(C(C(C=O)O)O)OIsomeric SMILESC([C@H]([C@@H](C=O)O)O)O
CAS No: 95-43-2 Synonyms: D-(?)-Threose MDL No: MFCD00043042 Chemical Formula: C4H8O4 Molecular Weight: 120.1References: 1. Beil. 1, IV, 4173