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:
Molecular Weight:
260.28
Beilstein:
84386
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.22
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![(3AR,5S,6S,6AR)-5-((R)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-2,2-DIMETHYLTETRAHYDROFURO[3,2-D][1,3]DIOXOL-6-OL AldrichCPR](/deepweb/assets/sigmaaldrich/product/structures/241/825/1c695a85-5c36-42d3-806a-30876a4dabac/640/1c695a85-5c36-42d3-806a-30876a4dabac.png)
grade
purum
Quality Level
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
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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.
Leonardo Guimarães de Oliveira et al.
Meat science, 155, 50-60 (2019-05-11)
The aim of this study was to determine the extent to which calpastatin (CASN) variants (based on two chromatographic peaks; CASN-P1 and CASN-P2) explain variation in μ-calpain autolysis, protein degradation, and changes in the sarcoplasmic proteome observed during postmortem aging
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