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

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-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 Number582-52-5
Product NameDiacetone-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 FormulaC12H20O6
Molecular Weight260.28 g/mol
InChIInChI=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 KeyKEJGAYKWRDILTF-JDDHQFAOSA-N
SMILESCC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C
SolubilitySoluble in DMSO
Synonyms1,2-5,6-di-O-isopropylidene-D-glucofuranose, 1,2-5,6-di-O-isopropylidene-D-glucofuranose, potassium salt, diacetone glucose
Canonical SMILESCC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C
Isomeric SMILESCC1(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.: C12H20O             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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