582-52-5 , 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose,
CAS:582-52-5
C12H20O6 / 260.28
MFCD00005544
1,2:5,6-二-O-异亚丙基-α-D-呋喃葡萄糖,
1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose, also known as diacetone-D-glucose (DAG), is a partially protected D-glucose sugar locked in the furanose form with isopropylidene protecting groups on the 1,2 and 5,6 positions. The unprotected 3 position is ready for a variety of chemical manipulations, such as alkylation, acylation or stereo-inversion. An orthogonal protecting group could be added to the 3 position to allow deprotection of an isopropylidene and therefore manipulations of the other hydroxyl groups. Diacetone-D-glucose has been used to make fluorinated hexopyranose glycolysis inhibitors useful in the treatment of brain tumours.
CAS Number | 582-52-5 |
Product Name | Diacetone-D-glucose |
IUPAC Name | (3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol |
Molecular Formula | C12H20O6 |
Molecular Weight | 260.28 g/mol |
InChI | 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 |
SMILES | CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C |
Solubility | Soluble in DMSO |
Synonyms | 1,2-5,6-di-O-isopropylidene-D-glucofuranose, 1,2-5,6-di-O-isopropylidene-D-glucofuranose, potassium salt, diacetone glucose |
Canonical SMILES | CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C |
Isomeric SMILES | CC1(OC[C@@H](O1)[C@@H]2[C@@H]([C@@H]3[C@H](O2)OC(O3)(C)C)O)C |
COA:
Product name: 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose; Diacetone-D-glucose
CAS: 582-52-5 M.F.: C12H20O6 M.W.: 260.28
Batch No: 20130308 Quantity:18.3 kg
Items | Standards | Results |
Appearance | White crystalline power | Positive |
Solubility | Soluble in CHCl3 and less soluble in petroleum ether | Complies |
Appearance of solution | Dissolve0.5 gin 10 ml of water, and the solution should be clear | Complies |
NMR and ESI-MS | Should comply | Complies |
Identification | IR and TLC | Positive |
Melting point | 105℃ ~110℃ | 108℃ ~110℃ |
Optical Activity [α]20/D (c=5 inwater) | -18° ~ -19° | -18.4° |
Loss Weight On Dryness | Max. 0.5% | Complies |
Residue on ignition | Max. 0.5% | 0.05% |
Heavy metal | Max. 20ppm | Complies |
TLC (15%H2SO4-C2H5OH) | One spot | Complies |
Assay | Min. 98% | 99.2% |
References:
1. Karakawa M, Nakatsubo F, Carbohydr. Res. 2002, 337, 10, p951
2. Hung SC, Thopate SR, Puranik R, Carbohydr. Res. 2001, 23, 331, p369
3. Berndt DF, Norris P, Tetrahedron Lett. 2002, 43, p3961
4. Beil. 31, p155
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