2039. d-Chalcose
Nomenclature
CAS number: 3150-28-5
4,6-Dideoxy-3-O-methyl-d-xylo-hexose; 4,6-dideoxy-3-O-methyl-d-glucose; lankavose. C7H14O4; mol wt 162.18.
C 51.84%, H 8.70%, O 39.46%.
Description and references
Component of chalcomycin and lankamycin, q.q.v. Prepn from chalcomycin and structure: Woo et al., J. Am. Chem. Soc. 83, 3352 (1961). Stereochemistry: Woo et al., ibid. 84, 1066 (1962); Foster et al., J. Chem. Soc. 1965, 2318. Synthesis: Kochetkov, Usov, Tetrahedron Lett. 1963, 519; McNally, Overend, Chem. Ind. (London) 1964, 2021; Lawton et al., Can. J. Chem. 47, 2899 (1969). Synthesis of dl-form: R. M. Srivastava, R. K. Brown, Can. J. Chem. 48, 830 (1970); K.Torssell, M. P. Tyagi, Acta Chem. Scand. B 31, 1 (1977); S. Danishefsky, J. F. Kerwin, J. Org. Chem. 47, 1597 (1982).
Properties
Crystals, mp 96-99°. [α]D24 +120° (2 min) → +97° (10 min) → +76° (3 hr and 26 hr) (c = 1.5 in water).Derivative
Methyl chalcoside.C8H16O4; mol wt 176.21.
C 54.53%, H 9.15%, O 36.32%.