D-Glucose

Catalog	BBC50997
CAS	50-99-7
Structure
Synonyms	(+)-Glucose,Anhydrous dextrose
IUPAC Name	(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
Molecular Weight	180.16
Molecular Formula	C6H12O6
Canonical SMILES	C([C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)O
InChI	InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6+/m0/s1
InChI Key	GZCGUPFRVQAUEE-SLPGGIOYSA-N
Melting Point	150-152 °C (lit.)
Purity	99%
Density	1.544 g/ml
Appearance	White powder
pH	5.0-7.0 (1M, H2O, 25°C)
pKa	12.43
Refractive Index	53 ° (C=10, H2O)
Solubility in Water	Soluble

Case Study

Synthesis and Corrosion Inhibition of Mild Steel by D-Glucose

Verma, C., Quraishi, M.A., Kluza, K., Makowska-Janusik, M., Olasunkanmi, L.O. and Ebenso, E.E., 2017. Scientific Reports, 7(1), p.44432.

D-glucose derivatives of dihydropyrido-[2,3-d:6,5-d']-dipyrimidine-2,4,6,8(1H,3H,5H,7H)-tetraone (GPHs) were synthesized and evaluated as corrosion inhibitors for mild steel in 1M HCl solution. Their effectiveness was studied using gravimetric analysis, electrochemical techniques, surface analysis, quantum chemical calculations, and Monte Carlo simulations.
Experimental Procedure:
The synthesis involved stirring 5 mL of an ethanol solution containing barbituric acid (2 mmol), glucose (1 mmol), aniline (1 mmol), and PTSA (0.1 g) at 50°C for 24 hours. After the reaction was completed, confirmed by TLC using EtOAc-MeOH as the eluent, the mixture was cooled to room temperature. The reaction mixture was then filtered, and the crude product was washed three times with ethanol (3 × 5 mL).

Synthesis of Azidoacetamide-Functionalized Pseudaminic Acid (Pse) Derivatives from D-Glucose

Vibhute, Amol M., et al. Chemistry-A European Journal 27.41 (2021): 10595-10600.

Pseudaminic acid (Pse) is a crucial prokaryotic monosaccharide present in both Gram-negative and Gram-positive bacteria, playing a significant role in their virulence by forming part of cell-surface-associated glycans or glycoproteins. This study reports the synthesis of azidoacetamide-functionalized Pse derivatives as potential metabolic labeling reagents. The synthesis utilized D-glucose (Glc) as a cost-effective and readily available chiral starting material.
Synthetic Strategy:
A straightforward synthetic route was developed starting from D-glucose to prepare azidoacetamide-functionalized Pse derivatives. Key steps included the inversion of the C3 and C5 alcohol groups of Glc through deoxyamination, introducing the nitrogen functionalities characteristic of Pse. The aldehyde group of Glc was reduced to form a methyl group, which subsequently became the C9 terminus of Pse, while the primary alcohol at C6 was oxidized to an aldehyde, enabling chain elongation.
Chain elongation was achieved using a Barbier reaction with a bromoallyl fragment, which introduced a C3 unit. Subsequent ozonolysis generated the keto functionality at the C2 position of Pse. This approach allowed selective functionalization of the two amino groups of Pse, enabling the attachment of either an acetamide or azidoacetamide group.
The synthesis produced N5- and N7-azidoacetamide-functionalized Pse derivatives in both lipophilic (ester-protected) and hydrophilic (deprotected) forms, providing versatile carbohydrate scaffolds for future applications.

Synthesis of Benzimidazoles via Oxidative Cyclization of D-Glucose with o-Phenylenediamines in Water

Raja, Dineshkumar, et al. The Journal of Organic Chemistry 85.17 (2020): 11531-11540.

D-Glucose serves as an efficient C1 synthon for the synthesis of benzimidazoles from o-phenylenediamines through an oxidative cyclization strategy. This method features broad functional group compatibility, utilizes a renewable methine source, achieves excellent yields within a short reaction time, and employs water as an environmentally friendly solvent.
Experimental Procedure:
In a 15 mL sealed tube, 1a-1zc (1.0 mmol), water (0.2 M), D-glucose (1.0 equiv), TBHP (70% in water, 1.0 mmol), and TfOH (0.2 mmol) were combined. The mixture was stirred at 100 °C for approximately 1 hour, monitored by TLC to confirm reaction completion. After cooling to room temperature, the reaction mixture was diluted with 10 mL of water and neutralized with NaHCO₃.
The aqueous layer was extracted with ethyl acetate (3 × 15 mL), and the combined organic layers were washed with brine (1 × 20 mL). The ethyl acetate layer was dried over Na₂SO₄, concentrated under reduced pressure, and the crude product was purified by column chromatography using a 1:1 ethyl acetate/hexane eluent. This process afforded pure 1H-benzimidazoles (3a-3zc) in yields ranging from 22% to 90%.