Title: Levoglucosenone

CAS Registry Number: 37112-31-5

CAS Name: (1S,5R)-6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one

Additional Names: 1,6-anhydro-3,4-dideoxy-b-D-glycero-hex-3-enopyranos-2-ulose; 1,6-anhydro-3,4-dideoxy-D3-b-D-pyranosen-2-one

Molecular Formula: C6H6O3

Molecular Weight: 126.11

Percent Composition: C 57.14%, H 4.80%, O 38.06%

Literature References: (-)-Form is a pyrolysis product of cellulose and cellulose-containing materials including pulp and paper waste products. Prepn from cellulosic materials: Y. Halpern et al., J. Org. Chem. 38, 204 (1973); and decompn reactions: F. Shafizadeh, P. P. S. Chin, Carbohydr. Res. 46, 149 (1976). Prepn from Kraft paper: eidem, ibid. 58, 79 (1977). Synthesis of (-)-form: M. Shibagaki et al., Chem. Lett. 1990, 307; of (+) and (-) enantiomers: T. Taniguchi et al., Synlett 1996, 971. MS analysis: Y. Halpern, J. P. Hoppesch, J. Org. Chem. 50, 1556 (1985). Electrochemistry: C. Z. Smith et al., J. Chem. Res. Synop. 1987, 88. Stereoselective reactivity: F. Shafizadeh et al., Carbohydr. Res. 71, 169 (1979). Cycloaddition reactions: idem et al., ibid. 114, 71 (1983); A. J. Blake et al., Tetrahedron 48, 8053 (1992). Michael addition reactions: M. G. Essig, Carbohydr. Res. 156, 225 (1986); A. V. Samet et al., 61, 8786 (1996). Applications in chiral carbohydrate synthesis: Y. Gelas-Mialhe et al., Heterocycles 24, 931 (1986); Z. J. Witczak, Pure Appl. Chem. 66, 2189 (1994); R. Blattner, D. M. Page, J. Carbohydr. Chem. 13, 27 (1994).

Properties: Faintly greenish-yellow liquid. nD25 1.5084. uv max (n-hexane): 211, 275 nm (log E1%1cm 2.82, 1.5). uv max (95% ethanol): 218, 275 nm (log E1%1cm 2.78, 1.5). [a]D25 -460° (c = 1.0 in CHCl3) (Halpern, 1973); also reported as [a]D31 -514.8° (c = 0.3 in CHCl3) (Taniguchi).

Optical Rotation: [a]D25 -460° (c = 1.0 in CHCl3) (Halpern, 1973); [a]D31 -514.8° (c = 0.3 in CHCl3) (Taniguchi).

Index of refraction: nD25 1.5084

Absorption maximum: uv max (n-hexane): 211, 275 nm (log E1%1cm 2.82, 1.5); uv max (95% ethanol): 218, 275 nm (log E1%1cm 2.78, 1.5)

Use: Chiral building block in organic synthesis.