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D7600

Sigma-Aldrich

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

98%

Sinónimos:

1,2,5,6-diisopropylidene-D-glucose, D-Glucose diacetonide, Diacetone-D-glucose

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About This Item

Fórmula empírica (notación de Hill):
C12H20O6
Número de CAS:
582-52-5
Peso molecular:
260.28
Beilstein/REAXYS Number:
84386
EC Number:
209-486-0
MDL number:
MFCD00005544
UNSPSC Code:
12352201
PubChem Substance ID:
24894140
NACRES:
NA.22

assay

98%

form

powder

optical activity

[α]20/D −18°, c = 1% in H2O

mp

109-113 °C (lit.)

SMILES string

[H][C@@]1(O[C@H]2O[C@@H](O[C@@H]2[C@H]1O)C(Cl)(Cl)Cl)[C@H]3COC(C)(C)O3

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

Application

1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose can be used as a starting material to prepare:
  • Biologically active L-acovenose, 6-deoxy-L-idose and, carbanucleoside enantiomers.
  • Vinyl ether-based chiral carbohydrate synthon by reacting with acetylene using superbase catalytic systems.
  • Fluoro-thiofuranosyl nucleosides of biological importance.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Benzyl bromide reagent grade, 98%

Sigma-Aldrich

B17905

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An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents
Tsoukala E, et al.
Bioorganic & Medicinal Chemistry, 15(9), 3241-3247 (2007)
Direct vinylation of glucose derivatives with acetylene
Trofimov BA, et al.
Tetrahedron, 63(47), 11661-11665 (2007)
E White et al.
Biomedical mass spectrometry, 9(9), 395-405 (1982-09-01)
Two isotope dilution mass spectrometric methods have been developed for the determination of D-glucose in human serum. Each uses a uniformly labeled (13C)glucose as the internal standard. The first method involves conversion of glucose into 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose and an extensive clean-up
Sumati Bhatia et al.
Biomacromolecules, 12(10), 3487-3498 (2011-08-13)
Sugar-PEG-based polymers were synthesized by enzymatic copolymerization of 4-C-hydroxymethyl-1,2-O-isopropylidene-β-L-threo-pentofuranose/4-C-hydroxymethyl-1,2-O-benzylidene-β-L-threo-pentofuranose/4-C-hydroxymethyl-1,2-O-isopropylidene-3-O-pentyl-β-L-threo-pentofuranose with PEG-600 dimethyl ester using Novozyme-435 (Candida antarctica lipase immobilized on polyacrylate). Carbohydrate monomers were obtained by the multistep synthesis starting from diacetone-D-glucose and PEG-600 dimethyl ester, which was in turn
T Z Csáky
Journal of medicine, 16(5-6), 575-586 (1985-01-01)
Based on a previous observation, it was postulated that dimethylsulfoxide (DMSO) acts as a carrier-model in the intestinal absorption of glucose and galactose (Csáky and Ho, 1966). It was further hypothetized that DMSO forms a loosely-bonded hydrophobic complex with the
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