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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The role of pyridoxal 5'-phosphate and orthophosphate in general acid-base catalysis by alpha-glucan phosphorylases.
H W Klein et al.
Progress in clinical and biological research, 144A, 147-160 (1984-01-01)
Patricia Wildberger et al.
Carbohydrate research, 356, 224-232 (2012-05-18)
Cellobiose phosphorylase from Cellulomonas uda (CuCPase) is shown to utilize D-glucal as slow alternative donor substrate for stereospecific glycosyl transfer to inorganic phosphate, giving 2-deoxy-α-D-glucose 1-phosphate as the product. When performed in D(2)O, enzymatic phosphorolysis of D-glucal proceeds with incorporation
H W Klein et al.
Biochemistry, 21(26), 6675-6684 (1982-12-21)
D-Glucal, containing a highly reactive double bond, can replace glucose 1-phosphate as the glucosyl donor in phosphorylase-catalyzed glucosyl transfer to a suitable oligo- or polysaccharide acceptor: D-glucal + Pi + (glucose)Pi leads to n 2-deoxy-alpha-D-glucosyl(glucose)n in equilibrium 2-deoxy-alpha-D-glucose-1-P + (glucose)n.
Y Nagumo et al.
Bioorganic & medicinal chemistry letters, 11(15), 2037-2040 (2001-07-17)
Monoclonal antibodies (mAbs), 4H2 and 6H7, were prepared previously using a protein conjugate of a 1:1 epimeric mixture of the synthetic ABC-ring fragments of ciguatoxin (CTX), 3 and 4. Here, the interactions of these mAbs with the fragments of CTX
Russell J Hewitt et al.
Chemical communications (Cambridge, England), 47(1), 421-423 (2010-09-21)
gem-Dibromocyclopropane 1, prepared from tri-O-benzyl-D-glucal, undergoes thermal and silver-promoted ring expansion in the presence of alcohols to give substituted oxepines. With further heating, ring contraction to highly substituted tetrahydrofurans follows. These represent C-furanosides, potentially useful as precursors to C-nucleosides and
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