D7600
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:
Molecular Weight:
260.28
UNSPSC Code:
12352201
NACRES:
NA.22
PubChem Substance ID:
EC Number:
209-486-0
Beilstein/REAXYS Number:
84386
MDL number:
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 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
assay
98%
form
powder
optical activity
[α]20/D −18°, c = 1% in H2O
mp
109-113 °C (lit.)
Quality Level
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
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)
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
Z Huang et al.
Methods in molecular biology (Clifton, N.J.), 20, 315-353 (1993-01-01)
Two sets of experimental protocols are given for the synthesis of 3',5'-bis-homodeoxyribonucleosides, building blocks for the synthesis of oligodeoxynucleotide analogs where the -O-PO2-O- groups are replaced by -CH2-S-CH2-, -CH2-SO-CH2-, and -CH2-SO2-CH2- units. Conditions are presented for joining these building blocks
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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