Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCR9245
MKCR4493
MKCP1509
MKCJ2379
MKCD8916

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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.
Tetrahedron, 47, 3895-3895 (1991)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service