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Merck

31460

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

Key Documents

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InChI key

KEJGAYKWRDILTF-JDDHQFAOSA-N

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

SMILES string

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

grade

purum

assay

≥98.0% (TLC)

optical activity

[α]20/D −11.5±1°, c = 5% in ethanol

mp

110-111 °C (lit.)

Quality Level

100

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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

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4674
BCCN1177
BCCH7612
BCBX7217
BCBV1353

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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
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
S C Hung et al.
Carbohydrate research, 331(4), 369-374 (2001-06-12)
A practical route toward the synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose is described. Key steps include the stereoselective hydrogenation of 6-deoxy-1,2:3,5-di-O-isopropylidene-alpha-D-xylo-hex-5-enofuranose, regioselective protection of 6-deoxy-1,2-O-isopropylidene-beta-L-idofuranose at 0-5, and epimerisation of 6-deoxy-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-beta-L-idofuranose at C-3.
A. Vasella et al.
Modern Synthetic Methods, 2, 173-173 (1980)
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