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D7600

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

Name: 1,2:5,6-Di-<I>O</I>-isopropylidene-α-<SC>D</SC>-glucofuranose
Brand: ALDRICH

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

UNSPSC Code:

12352201

NACRES:

NA.22

PubChem Substance ID:

24894140

EC Number:

209-486-0

Beilstein/REAXYS Number:

84386

MDL number:

MFCD00005544

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Properties

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

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

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