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390879

Sigma-Aldrich

1,2,3,4-Tetra-O-acetyl-β-D-glucopyranose

98%

Synonym(s):

1,2,3,4-Tetra-O-acetyl-beta-D-glucose

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About This Item

Empirical Formula (Hill Notation):
C14H20O10
CAS Number:
13100-46-4
Molecular Weight:
348.30
EC Number:
236-018-2
MDL number:
MFCD00063260
UNSPSC Code:
12352201
PubChem Substance ID:
24864350
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

optical activity

[α]20/D +11°, c = 6 in chloroform

mp

126-128 °C (lit.)

SMILES string

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

InChI

1S/C14H20O10/c1-6(16)20-11-10(5-15)24-14(23-9(4)19)13(22-8(3)18)12(11)21-7(2)17/h10-15H,5H2,1-4H3/t10-,11-,12+,13-,14-/m1/s1

InChI key

FEQXFAYSNRWXDW-RKQHYHRCSA-N

General description

1,2,3,4-Tetra-O-acetyl-β-ᴅ-glucopyranoseis a carbohydrate that is used in the synthesis of disaccharides and D-glucose6-phosphate.

Application

Phosphorylated derivatives have proven valuable in the study of substrates for inositol synthase, and for the preparation of anionic surfactants.

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)

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Beata Liberek et al.
Carbohydrate research, 341(13), 2275-2285 (2006-07-15)
The single-crystal X-ray diffraction and high-resolution 1H and 13C NMR spectral data for methyl 2,5-di-O-acetyl-beta-D-glucofuranosidurono-6,3-lactone and 1,2,5-tri-O-acetyl-beta-D-glucofuranurono-6,3-lactone are reported. The lactones were synthesized as byproducts of reactions carried out to obtain methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate. The conformations of these lactones in the
Yuriko Y Root et al.
Carbohydrate research, 337(21-23), 2343-2346 (2002-11-16)
The identity of the crystalline product formed by the acetylation of a mixture of methyl alpha- and beta-D-glucopyranuronates has been confirmed as being methyl 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranuronate (3), which agrees with the assignment from 1H NMR. The absolute configuration of compound 3
A Milius et al.
Carbohydrate research, 229(2), 323-336 (1992-05-22)
D-Glucose 3- and 6-[sodium 2-(perfluoro-hexyl or -octyl)ethyl phosphates) have been synthesized by condensation of 1,2,3,4,-tetra-O-acetyl-beta-D-glucopyranose and 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose with 2-(perfluoroalkyl)ethylphosphoroditriazolides followed by O-deacetylation or deacetalation. The structures of the compounds were established on the basis of 1H-, 19F-, 31P-, and 13C-NMR
Tetrahedron, 47, 3895-3895 (1991)
Wei Wang et al.
Glycoconjugate journal, 31(2), 133-143 (2013-11-13)
A group of fluorescent statistical glycopolymers, prepared via reversible addition-fragmentation chain-transfer (RAFT)-based polymerizations, were successfully employed in lectin-mediated bacterial binding studies. The resultant glycopolymers contained three different monomers: N-(2-hydroxyethyl) acrylamide (HEAA), N-(2-aminoethyl) methacrylamide (AEMA) and N-(2-glyconamidoethyl)-methacrylamides possessing different pendant sugars.
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