464058
D-Glucal
96%
Synonym(s):
1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol
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About This Item
Empirical Formula (Hill Notation):
C6H10O4
CAS Number:
Molecular Weight:
146.14
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352201
EC Number:
236-259-3
MDL number:
InChI key
YVECGMZCTULTIS-PBXRRBTRSA-N
InChI
1S/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6+/m1/s1
SMILES string
OC[C@H]1OC=C[C@@H](O)[C@@H]1O
assay
96%
form
solid
optical activity
[α]21/D −7°, c = 1.9 in H2O
impurities
<1% methyl alcohol
mp
58-60 °C (lit.)
storage temp.
2-8°C
Quality Level
Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Syed Khalid Yousuf et al.
The Journal of organic chemistry, 75(9), 3097-3100 (2010-04-13)
Novel one-pot three- and four-component transformations of D-glucal to furan-based hydroxy triazole glycoconjugates have been achieved by sequential addition of reagents in the presence of Cu(OTf)(2)-Cu powder as catalysts. In general the carbohydrate-derived products were formed with high diastereomeric purity.
A possible catalytic role of pyridoxal-5'-phosphate in a general acid base catalyzed reaction of D-glucal with glycogen phosphorylases.
E J Helmreich et al.
Progress in clinical and biological research, 102 Pt C, 23-35 (1982-01-01)
Xi-Kai Cui et al.
Carbohydrate research, 358, 19-22 (2012-08-03)
2-Deoxyglycosides were synthesized in high α-selectivity by the direct addition of alcohols to D-glucal and D-galactal catalyzed by TMSI and PPh(3). The acid labile isopropylidene group is tolerated under this condition.
Qi Chen et al.
Carbohydrate research, 342(11), 1405-1411 (2007-05-23)
A total synthesis of the 12-membered ring natural macrolide, sporiolide B, was achieved from D-glucal in 17 steps with 4.8% overall yield. The required stereochemical configuration at C-3 and C-5 in sporiolide B was easily introduced by applying a Mitsunobu
S Chiba et al.
Biochemistry, 27(5), 1464-1469 (1988-03-08)
Alpha-Glucosidases from Aspergillus niger, pig serum, ungerminated rice, buckwheat, and sugar beet seeds (but not from brewers' yeast or honeybee) were found to catalyze the hydration of D-glucal. Each reactive alpha-glucosidase, incubated with D-glucal in D2O, was shown to protonate
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