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Sigma-Aldrich

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

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:
84386
EC Number:
209-486-0
MDL number:
MFCD00005544
UNSPSC Code:
12352201
PubChem Substance ID:
57648572
NACRES:
NA.22

grade

purum

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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S. Iacono et al.
Organic Syntheses, 64, 57-57 (1986)
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
A. Vasella et al.
Modern Synthetic Methods, 2, 173-173 (1980)
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
Guylaine M Defossemont et al.
Carbohydrate research, 338(6), 563-565 (2003-04-02)
The synthesis and characterisation of a novel chiral bicyclic oxacaprolactone is reported. The choice of diisopropylidene-D-glucose as a starting material allowed selective introduction of the synthetic equivalent necessary for the formation of the seven-membered ring of the lactone, i.e., one
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