CAS 7784-54-5

α-D-Glucopyranose, 2-(acetylamino)-2-deoxy-, 1,3,4,6-tetraacetate

Description:

α-D-Glucopyranose, 2-(acetylamino)-2-deoxy-, 1,3,4,6-tetraacetate, commonly referred to as a derivative of glucosamine, is a carbohydrate compound characterized by its acetylated functional groups. This substance features a glucopyranose ring structure, which is a six-membered cyclic form of glucose, with specific modifications at the 2-position where an acetylamino group is present, and at the 1, 3, 4, and 6 positions where acetyl groups are attached. These modifications enhance its solubility and reactivity, making it useful in various biochemical applications, including as a building block in glycosylation reactions and in the synthesis of more complex carbohydrates. The presence of multiple acetyl groups contributes to its stability and influences its interaction with biological systems. This compound is typically white to off-white in appearance and is soluble in polar solvents. Its applications may extend to pharmaceuticals, biochemistry, and materials science, where it can serve as a precursor for further chemical transformations.

Formula: C₁₆H₂₃NO₁₀

InChI: InChI=1S/C16H23NO10/c1-7(18)17-13-15(25-10(4)21)14(24-9(3)20)12(6-23-8(2)19)27-16(13)26-11(5)22/h12-16H,6H2,1-5H3,(H,17,18)/t12-,13-,14-,15-,16+/m1/s1

InChI key: InChIKey=OVPIZHVSWNOZMN-QCODTGAPSA-N

SMILES: O(C(C)=O)[C@H]1[C@H](OC(C)=O)[C@@H](COC(C)=O)O[C@H](OC(C)=O)[C@@H]1NC(C)=O

Synonyms:

• 1,3,4,6-Tetra-O-acetyl-2-acetamido-2-deoxy-α-<span class="text-smallcaps">D</span>-glucopyranose
• 1,3,4,6-tetra-O-acetyl-2-(acetylamino)-2-deoxy-alpha-D-glucopyranose
• 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-α-<span class="text-smallcaps">D</span>-glucopyranose
• 2-Acetamido-2-deoxy-1,3,4,6-tetra-O-acetyl-α-<span class="text-smallcaps">D</span>-glucopyranose
• 2-Acetamido-2-deoxy-alpha-D-glucose 1,3,4,6-tetraacetate
• 2-Acetamido-2-deoxy-α-<span class="text-smallcaps">D</span>-glucopyranose 1,3,4,6-tetraacetate
• 3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate
• Glucopyranose, 2-acetamido-2-deoxy-, 1,3,4,6-tetraacetate, α-<span class="text-smallcaps">D</span>-
• NSC 231931
• α-<span class="text-smallcaps">D</span>-Glucopyranose, 2-(acetylamino)-2-deoxy-, 1,3,4,6-tetraacetate
• 2-Acetamido-2-deoxy-α-D-glucopyranose 1,3,4,6-tetraacetate
• Glucopyranose, 2-acetamido-2-deoxy-, 1,3,4,6-tetraacetate, α-D-
• 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranose
• α-D-Glucopyranose, 2-(acetylamino)-2-deoxy-, 1,3,4,6-tetraacetate

2-ACETAMIDO-2-DEOXY-1,3,4,6-TETRA-O-ACETYL-α-D-GLUCOPYRANOSE

CAS: 7784-54-5

Formula: C₁₆H₂₃NO₁₀

Purity: 97%

Color and Shape: Solid

Molecular weight: 389.3545

Ref: IN-DA00G2QJ

α-D-Glucosamine Pentaacetate

CAS: 7784-54-5

α-D-Glucosamine Pentaacetate

Purity: 98%

Molecular weight: 389.35g/mol

Ref: 54-OR1015496

α-D-Glucosamine Pentaacetate

CAS: 7784-54-5

Molecular weight: 389.35

Ref: 7W-GC6490

α-D-Glucosamine Pentaacetate

CAS: 7784-54-5

Formula: C₁₆H₂₃NO₁₀

Purity: >98.0%(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 389.36

Ref: 3B-A3380

α-D-Glucosamine Pentaacetate

Controlled Product

CAS: 7784-54-5

Applications α-D-Glucosamine Pentaacetate is a protected form of glucosamine
References Cudic, P., et al.: Bioorg. Med. Chem. Lett., 11, 3107 (2001),

Formula: C₁₆H₂₃NO₁₀

Color and Shape: Neat

Molecular weight: 389.35

Ref: TR-G515001

α-D-Glucosamine pentaacetate

CAS: 7784-54-5

Alpha-D-glucosamine pentaacetate is a carbohydrate that is a member of the glycoconjugates family. It is an acetylated form of alpha-D-glucosamine and is used in the synthesis of glycoproteins and glycosaminoglycans. Alpha-D-Glucosamine pentaacetate has been shown to be an effective inhibitor of methylation reactions. It can also be used as a fluorinating agent in organic synthesis or Click chemistry, which involves the reaction between an azide group and an alkyne group. Alpha-D-Glucosamine pentaacetate has been shown to be a potent antiviral agent against herpes simplex virus 1 (HSV1) by blocking viral adsorption and penetration into cells, inhibiting DNA replication, and reducing viral titers.

Formula: C₁₆H₂₃NO₁₀

Molecular weight: 389.36 g/mol

Ref: 3D-G-2960

2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-a-D-glucopyranose

CAS: 7784-54-5

2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-a-D-glucopyranose (2AAT) is a synthetic nucleoside that binds to the same sequence of n-acetylgalactosamine in the cell wall of Gram positive bacteria. It was found to be effective against bacterial strains that produce beta lactamase enzymes. 2AAT has been shown to inhibit the growth of Gram positive bacteria and is able to penetrate tissues. It also prevents bacterial DNA gyrase and topoisomerase IV from binding with their respective substrates. 2AAT is made up of four parts: two ribose molecules, one deoxyribose molecule and one acetamido group. This last part is what makes it bind to the bacterial cell wall and inhibits protein synthesis by preventing mRNA from being translated into proteins.

Formula: C₁₆H₂₃NO₁₀

Purity: Min. 98 Area-%

Color and Shape: White Powder

Molecular weight: 389.36 g/mol

Ref: 3D-MA07519

2-ACETAMIDO-2-DEOXY-1,3,4,6-TETRA-O-ACETYL-α-D-GLUCOPYRANOSE

CAS: 7784-54-5

Purity: 97%

Molecular weight: 389.3569946

Ref: 10-F863745