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G2354

Sigma-Aldrich

α-D(+)-Glucose pentaacetate

99%

Synonym(s):

1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose

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About This Item

Empirical Formula (Hill Notation):
C16H22O11
CAS Number:
604-68-2
Molecular Weight:
390.34
Beilstein:
98852
EC Number:
210-073-2
MDL number:
MFCD00064071
UNSPSC Code:
12164502
PubChem Substance ID:
24895094
NACRES:
NA.22

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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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
GHS07

Signal Word

Warning

Hazard Statements

H317

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Analysis of polysaccharides and monosaccharides in the root mucilage of maize (Zea mays L.) by gas chromatography
HI Osborn
Journal of Chromatography A, 831, 267-276 (1999)
Acetate groups as probes of the stereochemistry of carbohydrates: a vibrational circular dichroism study
PK Bose
Carbohydrate Research, 322, 135-141 (1999)
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)
F Ponticelli et al.
Carbohydrate research, 330(4), 459-468 (2001-03-28)
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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