CAS 51450-09-0

β-D-Glucopyranose, 2-(acetylamino)-2-deoxy-1-thio-, 3,4,6-triacetate

Description:

β-D-Glucopyranose, 2-(acetylamino)-2-deoxy-1-thio-, 3,4,6-triacetate, commonly referred to as a derivative of glucosamine, is a modified sugar molecule characterized by the presence of an acetylamino group and thio functionality at the 2-position, along with three acetyl groups at the 3, 4, and 6 positions. This compound is typically a white to off-white solid and is soluble in organic solvents, reflecting its acetylated nature. The presence of the thio group introduces unique reactivity, making it useful in various synthetic applications, particularly in carbohydrate chemistry and biochemistry. Its structural modifications enhance its biological activity and potential applications in drug development, particularly in targeting glycosylation processes. The compound's molecular structure contributes to its stability and reactivity, making it a valuable intermediate in the synthesis of more complex carbohydrate derivatives. As with many sugar derivatives, it may exhibit specific optical activity, which can be utilized in analytical techniques to confirm its identity and purity.

Formula: C₁₄H₂₁NO₈S

InChI: InChI=1S/C14H21NO8S/c1-6(16)15-11-13(22-9(4)19)12(21-8(3)18)10(23-14(11)24)5-20-7(2)17/h10-14,24H,5H2,1-4H3,(H,15,16)/t10-,11-,12-,13-,14+/m1/s1

InChI key: InChIKey=NABDIVBRJQHAOY-KSTCHIGDSA-N

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

Synonyms:

• (2R,3S,4R,5R,6S)-5-Acetamido-2-(acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4-diyl diacetate
• 2-Acetamido-2-deoxy-1-thio-β-d-glucopyranose 3,4,6-triacetate
• 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-β-<span class="text-smallcaps">D</span>-glucopyranose
• 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-<span class="text-smallcaps">D</span>-glucopyranose
• 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-1-thio-beta-D-glucopyranose
• <span class="text-smallcaps">D</span>-Glucose, 2-acetamido-2-deoxy-1-thio-, 3,4,6-triacetate
• β-<span class="text-smallcaps">D</span>-Glucopyranose, 2-(acetylamino)-2-deoxy-1-thio-, 3,4,6-triacetate
• β-D-Glucopyranose, 2-(acetylamino)-2-deoxy-1-thio-, 3,4,6-triacetate
• 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranose
• D-Glucose, 2-acetamido-2-deoxy-1-thio-, 3,4,6-triacetate
• 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-thioglucopyranose

CAS: 51450-09-0

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-thioglucopyranose is a Glycosylation reagent that is used in the synthesis of complex carbohydrates. It can be methylated and fluorinated. 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--bD thioglucopyranose has been shown to be a useful reagent for the synthesis of oligosaccharides. The purity of this compound is >98%. Custom synthesis is available on request.

Formula: C₁₄H₂₁NO₈S

Purity: Min. 95%

Molecular weight: 363.38 g/mol

Ref: 3D-MA10926