1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose

Name: 1,2:5,6-Di-<I>O</I>-isopropylidene-α-<SC>D</SC>-glucofuranose
Brand: ALDRICH

purum, ≥98.0% (TLC)

Synonym(s):

D-Glucose diacetonide, Diacetone-D-glucose

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₂₀O₆

CAS Number:

582-52-5

Molecular Weight:

260.28

Beilstein/REAXYS Number:

84386

EC Number:

209-486-0

MDL number:

MFCD00005544

UNSPSC Code:

12352201

PubChem Substance ID:

57648572

NACRES:

NA.22

Key Documents

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grade

purum

Quality Level

100

assay

≥98.0% (TLC)

optical activity

[α]20/D −11.5±1°, c = 5% in ethanol

mp

110-111 °C (lit.)

SMILES string

CC1(C)OC[C@@H](O1)[C@H]2O[C@@H]3OC(C)(C)O[C@@H]3[C@H]2O

InChI

1S/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3/t6-,7+,8-,9-,10-/m1/s1

Inchi Key

KEJGAYKWRDILTF-JDDHQFAOSA-N

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Other Notes

Important protected derivative of glucose; the 3-OH group can be directly manipulated, the 5,6-O-isopropylidene protection is selectively cleavable; oxidation and reduction of the 3-OH leads to an allofuranose derivative; review[1][2]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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A Chemical Genetics Screen Reveals Influence of p38 Mitogen-Activated Protein Kinase and Autophagy on Phagosome Development and Intracellular Replication of Brucella neotomae in Macrophages.

Yoon-Suk Kang et al.

Infection and immunity, 87(8) (2019-06-05)

Brucella is an intracellular bacterial pathogen that causes chronic systemic infection in domesticated livestock and poses a zoonotic infectious risk to humans. The virulence of Brucella is critically dependent on its ability to replicate and survive within host macrophages. Brucella

S. Iacono et al.

Organic Syntheses, 64, 57-57 (1986)

A. Vasella et al.

Modern Synthetic Methods, 2, 173-173 (1980)

Oligonucleotide analogs with dimethylenesulfide, -sulfoxide, and -sulfone groups replacing phosphodiester linkages.

Z Huang et al.

Methods in molecular biology (Clifton, N.J.), 20, 315-353 (1993-01-01)

Two sets of experimental protocols are given for the synthesis of 3',5'-bis-homodeoxyribonucleosides, building blocks for the synthesis of oligodeoxynucleotide analogs where the -O-PO2-O- groups are replaced by -CH2-S-CH2-, -CH2-SO-CH2-, and -CH2-SO2-CH2- units. Conditions are presented for joining these building blocks

The accurate determination of serum glucose by isotope dilution mass spectrometry--two methods.

E White et al.

Biomedical mass spectrometry, 9(9), 395-405 (1982-09-01)

Two isotope dilution mass spectrometric methods have been developed for the determination of D-glucose in human serum. Each uses a uniformly labeled (13C)glucose as the internal standard. The first method involves conversion of glucose into 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose and an extensive clean-up

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