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316555

Sigma-Aldrich

1,6-Anhydro-β-D-glucose

99%

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Synonym(s):
Levoglucosan
Empirical Formula (Hill Notation):
C6H10O5
CAS Number:
Molecular Weight:
162.14
Beilstein:
80998
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

powder or crystals

optical activity

[α]18/D −66°, c = 1 in H2O

color

beige

mp

182-184 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

SMILES string

O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1O

InChI

1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1

InChI key

TWNIBLMWSKIRAT-VFUOTHLCSA-N

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Application

1,6-Anhydro-β-D-glucose (Levoglucosan) can be used as a precursor for the synthesis of:
  • 1,6-anhydro-2,4-dideoxy-β-D-glycerohexopyranos-3-ulose.
  • Quasi-linear polyglucose (PGlc) via cationic ring-opening polymerization.
  • Polynitrogenated analogs of glucopyranoses.
  • 3-deoxy-3-fluorogalactopyranose and acetylated 4-deoxy-4-fluorogalactopyranose.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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  5. What is the method of manufacture for product 316555, 1,6-Anhydro-β-D-glucose?

    Product 316555, 1,6-Anhydro-β-D-glucose, is manufactured by the pyrolysis of starch.  The solvents used in the process are water, ethanol, and methanol.

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Synthesis of Protected 3-Deoxy-3-fluoro-and 4-Deoxy-4-fluoro-d-galactopyranosides from Levoglucosan
Laine D, et al.
The Journal of Organic Chemistry, 82(9), 4986-4992 (2017)
Dimitra Balla et al.
Environmental science and pollution research international, 25(13), 12191-12205 (2017-09-10)
Two classes of polar organic compounds, dicarboxylic acids (DCAs) and sugars/sugar anhydrides (S/SAs), were measured in airborne particulate matter in the area of Thessaloniki, northern Greece. The target compounds were measured simultaneously in two particle fractions PM10 and PM2.5 during
The controlled synthesis of polyglucose in one-dimensional coordination nanochannels
Kobayashi Y, et al.
Chemical Communications (Cambridge, England), 52(29), 5156-5159 (2016)
F Mashayekhy Rad et al.
Chemosphere, 211, 617-623 (2018-08-11)
In the present study, a methodology involving hydrophilic interaction liquid chromatography (HILIC) and electrospray (ESI) tandem mass spectrometry (MS/MS) was developed for measurement of anhydrous monosaccharides as markers for wood burning in atmospheric aerosols, PM10. No extensive sample preparation, other
Bret A Schichtel et al.
Environmental science & technology, 51(17), 9846-9855 (2017-08-02)
Carbonaceous compounds are a significant component of fine particulate matter and haze in national parks and wilderness areas where visibility is protected, i.e., class I areas (CIAs). The Regional Haze Rule set the goal of returning visibility in CIAs on

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