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G2354

Sigma-Aldrich

α-D(+)-Glucose pentaacetate

99%

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Synonym(s):
1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose
Empirical Formula (Hill Notation):
C16H22O11
CAS Number:
Molecular Weight:
390.34
Beilstein:
98852
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

optical activity

[α]20/D ≥+98°, c = 1 in ethanol

mp

109-111 °C (lit.)

SMILES string

CC(=O)OC[C@H]1O[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI

1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16+/m1/s1

InChI key

LPTITAGPBXDDGR-LJIZCISZSA-N

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This Item
134031104477A1750
mp

109-111 °C (lit.)

mp

143-144 °C (lit.)

mp

115-117 °C (lit.)

mp

88.5 °C ((191.3 °F ))

optical activity

[α]20/D ≥+98°, c = 1 in ethanol

optical activity

[α]20/D +8.6°, c = 1.5% in chloroform, [α]24/D +23°, c = 1 in chloroform

optical activity

[α]20/D +5.8°, c = 2.2 in chloroform

optical activity

[α]25/D 188 to 202 °, c = 1 in chloroform

General description

α-D(+)-Glucose pentaacetate also known as 1,2,3,4,6-penta-O-acetyl-α-D-glucopyranose, is an acetylated sugar that has wide applications in organic synthesis.

Application

α-D(+)-Glucose pentaacetate is used as a model compound to study the stereochemistry of carbohydrates through spectroscopic techniques such as Vibrational circular dichroism (VCD). Additionally, it has been used as a standard in the analysis of monosaccharide and polysaccharide components by gas chromatography.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Journal of Chromatography A, 831, 267-276 (1999)
Acetate groups as probes of the stereochemistry of carbohydrates: a vibrational circular dichroism study
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W J Malaisse et al.
Archives of biochemistry and biophysics, 381(1), 61-66 (2000-10-06)
Hepatocytes from fed rats were incubated for 120 min in the presence of alpha-D-[1,2-13C]glucose pentaacetate (1.7 mM), both D-[1,2-13C]glucose (1.7 mM) and acetate (8.5 mM), alpha-D-glucose penta[2-13C]acetate (1.7 mM), or D-[1,2-13C]glucose (8.3 mM). The amounts of 13C-enriched L-lactate and D-glucose
Monosaccharide esters: new tools in biomedical research.
W J Malaisse
Molecular genetics and metabolism, 65(2), 129-142 (1998-10-27)
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We describe the synthesis of some 3-tert-butyl-4-hydroxyphenyl D-glycopyranosides by reaction of tert-butylhydroquinone with beta-D-pentaacetyl-glucose, beta-D-pentaacetyl-galactose, 2-acetamido- and 3,4,6-tri-O-acetyl-2-butanamido-2-deoxy-beta-D-glucopyranosyl chlorides as well as the formation of anomeric 3-tert-butyl-4-hydroxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-eno-pyranosides by reaction between tert-butylhydroquinone and 3,4,6-tri-O-acetyl-D-glucal. All compounds, except 3-tert-butyl-4-hydroxyphenyl alpha- and

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