1, 2:5, 6-Di-O-isopropylidene-?-D-glucofuranose, CAS:582-52-5

1,2:5,6-Di-O-isopropylidene-?-D-glucofuranose, 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 Number582-52-5Product NameDiacetone-D-glucoseIUPAC 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-olMolecular FormulaC12H20O6Molecular Weight260.28 g/molInChIInChI=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/s1InChI KeyKEJGAYKWRDILTF-JDDHQFAOSA-NSMILESCC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)CSolubilitySoluble in DMSOSynonyms1,2-5,6-di-O-isopropylidene-D-glucofuranose, 1,2-5,6-di-O-isopropylidene-D-glucofuranose, potassium salt, diacetone glucoseCanonical SMILESCC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)CIsomeric SMILESCC1(OC[C@@H](O1)[C@@H]2[C@@H]([C@@H]3[C@H](O2)OC(O3)(C)C)O)CCOA:Product name:?1,2:5,6-Di-O-isopropylidene-?-D-glucofuranose; Diacetone-D-glucose
CAS: 582-52-5??????????????M.F.:?C12H20O6??????????????M.W.:?260.28Batch No: 20130308? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ??Quantity:18.3 kgItemsStandardsResultsAppearanceWhite crystalline powerPositiveSolubilitySoluble in CHCl3?andless soluble in petroleum etherCompliesAppearance of solutionDissolve0.5 gin 10 ml of water,and?the solution should be clearCompliesNMR and ESI-MSShould complyCompliesIdentificationIR and TLCPositiveMelting point105??~110?108??~110?Optical Activity[?]20/D (c=5 inwater)-18??~ -19?-18.4?Loss Weight On DrynessMax. 0.5%CompliesResidue on ignitionMax. 0.5%0.05%Heavy metalMax. 20ppmCompliesTLC?(15%H2SO4-C2H5OH)One spotCompliesAssayMin. 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