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464058

Sigma-Aldrich

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:
13265-84-4
Molecular Weight:
146.14
EC Number:
236-259-3
MDL number:
MFCD09039277
UNSPSC Code:
12352201
PubChem Substance ID:
24870132
NACRES:
NA.22

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

SMILES string

OC[C@H]1OC=C[C@@H](O)[C@@H]1O

InChI

1S/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6+/m1/s1

InChI key

YVECGMZCTULTIS-PBXRRBTRSA-N

Application

Important building block for both solution- and solid-phase synthesis of oligosaccharides.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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B Evers et al.
Bioorganic & medicinal chemistry, 5(5), 857-863 (1997-05-01)
Maltopentaose was immobilized on silica gel and used as a recyclable primer in the reaction of glycogen phosphorylase with D-glucal. An improved method to obtain 2-deoxy-alpha-D-arabino-hexopyranosyl phosphate (4) by using this catalyst as well as the specific synthesis of low
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.
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)
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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