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316555

Sigma-Aldrich

1,6-Anhydro-β-D-glucose

99%

Synonym(s):

Levoglucosan

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About This Item

Empirical Formula (Hill Notation):
C6H10O5
CAS Number:
498-07-7
Molecular Weight:
162.14
Beilstein:
80998
EC Number:
207-855-0
MDL number:
MFCD00063248
UNSPSC Code:
12352201
PubChem Substance ID:
24859027
NACRES:
NA.22

Quality Level

200

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCG6781
BCCF2591
BCCB7145
BCBW4707
BCBV6180

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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)
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
The controlled synthesis of polyglucose in one-dimensional coordination nanochannels
Kobayashi Y, et al.
Chemical Communications (Cambridge, England), 52(29), 5156-5159 (2016)
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
Practical synthesis of 1, 6-anhydro-2, 4-dideoxy-β -D-glycero-hexopyranos-3-ulose from levoglucosan
Belyk K, et al.
The Journal of Organic Chemistry, 65(8), 2588-2590 (2000)
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