582-52-5 , 1,2:5,6-二-O-异亚丙基-α-D-呋喃葡萄糖, CAS:582-52-5

582-52-5 , 1,2:5,6-二-O-异亚丙基-α-D-呋喃葡萄糖,
1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose,
CAS:582-52-5
C12H20O6 / 260.28
MFCD00005544

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

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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