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Merck
CN

285943

β-D-Glucose pentaacetate

98%

Synonym(s):

beta-D-Glucose pentaacetate, 1,2,3,4,6-Penta-O-acetyl-β-D-glucopyranose

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About This Item

Empirical Formula (Hill Notation):
C16H22O11
CAS Number:
604-69-3
Molecular Weight:
390.34
UNSPSC Code:
12352201
NACRES:
NA.22
PubChem Substance ID:
24857226
EC Number:
210-074-8
Beilstein/REAXYS Number:
98851
MDL number:
MFCD00006597

Key Documents

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Product Name

β-D-Glucose pentaacetate, 98%

InChI key

LPTITAGPBXDDGR-IBEHDNSVSA-N

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

SMILES string

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

assay

98%

form

powder

optical activity

[α]20/D +4.2°, c = 1 in chloroform

mp

130-132 °C (lit.)

Quality Level

100

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6319V
WXBF2734V
WXBD5873V
WXBD0461V
STBG1900V

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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
A Bastida et al.
Bioorganic & medicinal chemistry letters, 9(4), 633-636 (1999-03-31)
Penta-O-acetyl-alpha-D-glucopyranose was selectively deacetylated in aqueous media by lipases from Candida cilindracea (CCL) adsorbed on octyl-agarose support. Enzymatic hydrolyses was regioselective at the 4-position under neutral pH and towards the 6 position under acidic conditions. This enzymatic approach allows the
W J Malaisse
Acta clinica Belgica, 57(2), 49-52 (2002-08-03)
The first report dealing with the use of monosaccharide esters as new tools in biomedicine was published in 1997 (1). This topic was first reviewed in 1998 (2). The major aim of the present report is to briefly evoke the
Shaji K Chacko et al.
Journal of applied physiology (Bethesda, Md. : 1985), 104(4), 944-951 (2008-01-12)
We report a new method to measure the fraction of glucose derived from gluconeogenesis using gas chromatography-mass spectrometry and positive chemical ionization. After ingestion of deuterium oxide by subjects, glucose derived from gluconeogenesis is labeled with deuterium. Our calculations of
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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