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CAS No 37112-31-5 , 6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one,(1S,5R)-

  • Name: 6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one,(1S,5R)-
  • Synonyms: 6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one,(1S)-;6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one,(1S,5R)-; Levoglucosenone;
  • CAS Registry Number:
  • Flash Point: 98.2°C
  • Boiling Point: 254.4°Cat760mmHg
  • Density: 1.329g/cm3
  • Refractive index: 1.516
  • Flash Point: 98.2°C
  • Molecular Weight: 126.11
  • InChI: InChI=1/C6H6O3/c7-5-2-1-4-3-8-6(5)9-4/h1-2,4,6H,3H2/t4?,6-/m1/s1
  • Molecular Formula: C6H6O3
  • Molecular Structure:CAS No:37112-31-5 6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one,(1S,5R)-
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37112-31-5 LEVOGLUCOSENONE

  • Germany CHEMOS GmbH [Manufacturer]
  • Tel: 0049 9402/9336 0
  • Fax: 0049 9402/9336 13
  • Address: CHEMOS GmbH
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    93128 Regenstauf
    Germany null,nullGermany
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37112-31-5 A2047 LEVOGLUCOSENONE

  • United Kingdom Carbosynth Limited [Manufacturer]
  • Tel: +44 (0)1635 578444
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  • Address: Carbosynth Limited
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    Compton
    Berkshire
    RG20 6NE
    UK null,nullUnited Kingdom
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37112-31-5 LEVO-GLUCOSENONE

  • United States Equinox Chemicals, LLC [Manufacturer]
  • Tel: 877-815-9021/ 229-420-3886
  • Fax: 208-567-2370
  • Address: Equinox Chemicals, LLC
    1909 West Oakridge Drive
    Albany, Georgia 31707 null,nullUnited States
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37112-31-5 LEVOGLUCOSENONE

  • Canada LC Scientific Inc. [Manufacturer]
  • Tel: 905-669-0017
  • Fax: 905-669-0193
  • Address: LC Scientific Inc.
    5-150 Connie Crescent
    Concord, Ontario
    L4K 1L9, Canada null,nullCanada
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References of 6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one,(1S,5R)-
Title: Levoglucosenone
CAS Registry Number: 37112-31-5
CAS Name: (1S,5R)-6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one
Synonyms: 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.