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D7600

Sigma-Aldrich

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

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H20O6
CAS Number:
582-52-5
Molecular Weight:
260.28
Beilstein:
84386
EC Number:
209-486-0
MDL number:
MFCD00005544
UNSPSC Code:
12352201
PubChem Substance ID:
24894140
NACRES:
NA.22

Quality Level

200

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 Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK6751
MKBZ5297V
MKBT8903V
MKBK4060V
MKBD7675V

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Direct vinylation of glucose derivatives with acetylene
Trofimov BA, et al.
Tetrahedron, 63(47), 11661-11665 (2007)
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)
Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3, 5-bishydroxymethyl cyclopentanol from d-glucose
Roy BG, et al.
Tetrahedron Letters, 47(50), 8821-8825 (2006)
Guylaine M Defossemont et al.
Carbohydrate research, 338(6), 563-565 (2003-04-02)
The synthesis and characterisation of a novel chiral bicyclic oxacaprolactone is reported. The choice of diisopropylidene-D-glucose as a starting material allowed selective introduction of the synthetic equivalent necessary for the formation of the seven-membered ring of the lactone, i.e., one
S C Hung et al.
Carbohydrate research, 331(4), 369-374 (2001-06-12)
A practical route toward the synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose is described. Key steps include the stereoselective hydrogenation of 6-deoxy-1,2:3,5-di-O-isopropylidene-alpha-D-xylo-hex-5-enofuranose, regioselective protection of 6-deoxy-1,2-O-isopropylidene-beta-L-idofuranose at 0-5, and epimerisation of 6-deoxy-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-beta-L-idofuranose at C-3.
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