CAS 74808-10-9

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

Description:

α-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) is a derivative of glucose, specifically an acetylated form of α-D-glucopyranose. This compound features multiple acetyl groups at the 2, 3, 4, and 6 positions, which enhances its lipophilicity and stability compared to unmodified glucose. The presence of the 1-(2,2,2-trichloroethanimidate) moiety indicates that it is designed for specific reactivity, likely in glycosylation reactions, making it useful in synthetic organic chemistry and carbohydrate chemistry. The trichloroethanimidate group serves as a leaving group, facilitating the formation of glycosidic bonds. This compound is typically a white to off-white solid and is soluble in organic solvents, reflecting its modified structure. Its applications may include use in the synthesis of oligosaccharides or glycoproteins, where controlled glycosylation is essential. As with many chemical substances, proper handling and safety precautions are necessary due to potential hazards associated with its components.

Formula: C₁₆H₂₀Cl₃NO₁₀

InChI: InChI=1S/C16H20Cl3NO10/c1-6(21)25-5-10-11(26-7(2)22)12(27-8(3)23)13(28-9(4)24)14(29-10)30-15(20)16(17,18)19/h10-14,20H,5H2,1-4H3/t10-,11-,12+,13-,14-/m1/s1

InChI key: InChIKey=IBUZGVQIKARDAF-RKQHYHRCSA-N

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

Synonyms:

• 2,3,4,6-Tetra-O-Acetyl-Alpha-D-Glucopyranosyl Trichloroacetimidate
• 2,3,4,6-Tetra-O-acetyl-a-D-glucopyranosyltrichloroacetimidate
• 2,3,4,6-Tetra-O-acetyl-α-<span class="text-smallcaps">D</span>-glucopyranosyl trichloroacetimidate
• Tetra-O-acetyl-α-<span class="text-smallcaps">D</span>-glucose trichloroacetimidate
• α-<span class="text-smallcaps">D</span>-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)
• α-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)
• 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• Tetra-O-acetyl-α-D-glucose trichloroacetimidate

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate

CAS: 74808-10-9

Formula: C₁₆H₂₀Cl₃NO₁₀

Purity: 98%

Color and Shape: Solid

Molecular weight: 492.6897

Ref: IN-DA005SXS

α-D-Glucopyranose, 2,3,4,6-tetraacetate

CAS: 74808-10-9

α-D-Glucopyranose, 2,3,4,6-tetraacetate

Purity: 98%

Molecular weight: 492.69g/mol

Ref: 54-OR1007755

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate

CAS: 74808-10-9

Molecular weight: 492.69

Ref: 7W-GC3403

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate

Controlled Product

CAS: 74808-10-9

Stability Hygroscopic, Water Sensitive
Applications 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate is a useful reagent for the synthesis of natural glycosides (Isosyringinoside and glucopyranosyL-​glucopyranosyl-​hydroxy phenylethanol I).
References Dong, H., et al.: Carbohydrate Research, 499, 108200 (2021)

Formula: C₁₆H₂₀Cl₃NO₁₀

Color and Shape: Neat

Molecular weight: 492.69

Ref: TR-T281450

2,3,4,6-Tetra-O-acetyl-a-D-glucopyranosyl trichloroacetimidate

CAS: 74808-10-9

2,3,4,6-Tetra-O-acetyl-a-D-glucopyranosyl trichloroacetimidate (2TG) is a mannose targeting agent that can be used to target specific cells in the body. This compound has been shown to inhibit the growth of cancer cells and induce photodynamic therapy. 2TG is a conjugate that consists of a 6-phosphate group attached to an acetylated mannose molecule. The 6-phosphate group is an important feature for tumor targeting, as it allows for the attachment of other molecules such as monoclonal antibodies and drugs. 2TG functions by binding with high affinity to glycoproteins on the surface of cancer cells and animal tissues. These glycoproteins are found in large quantities on the surface of cancer cells and animal tissue, which makes them good targets for anti-cancer drug development.

Formula: C₁₆H₂₀Cl₃NO₁₀

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 492.69 g/mol

Ref: 3D-MT04863

α-D-Glucopyranose, 2,3,4,6-tetraacetate

CAS: 74808-10-9

Purity: 98%

Molecular weight: 491.02

Ref: 10-F554478