(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl triacetate
$250.00
CAS No.: 19879-84-6
Catalog No.: 195038
Purity: 95%
MF: C14H20O9S
MW: 364.372
Storage: 2-8 degree Celsius
SMILES: C(C)(=O)O[C@H]1[C@H](S)O[C@@H]([C@H]([C@@H]1OC(C)=O)OC(C)=O)COC(C)=O
Catalog No.: 195038
Purity: 95%
MF: C14H20O9S
MW: 364.372
Storage: 2-8 degree Celsius
SMILES: C(C)(=O)O[C@H]1[C@H](S)O[C@@H]([C@H]([C@@H]1OC(C)=O)OC(C)=O)COC(C)=O
(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl triacetate; CAS No.: 19879-84-6; (2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl triacetate. PROPERTIES: (2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl triacetate appears as a white to off-white crystalline solid with a slight acetic odor. Its molecular formula is C14H19O9S, corresponding to a molecular weight of approximately 369.37 g/mol. The compound exhibits a melting point in the range of 80-85 C and demonstrates moderate solubility in common organic solvents such as methanol, ethyl acetate, and dichloromethane while being sparingly soluble in water. It is sensitive to moisture and heat, which may cause hydrolysis and decomposition. Proper storage requires keeping it in a tightly sealed, amber glass container in a cool, dry location away from direct sunlight and heat sources. The temperature should be maintained below 10 C if possible. Safety precautions include using chemical-resistant gloves, safety goggles, and lab coats to prevent skin absorption and inhalation of dust. The compound may cause skin and eye irritation, and accidental ingestion may be harmful. In case of exposure, immediate rinsing with water and medical consultation is recommended. APPLICATIONS: (2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl triacetate serves as a specialized intermediate in carbohydrate chemistry, particularly valuable in the synthesis of nucleoside analogs and glycosylation reagents. Its protected hydroxyl and thiol groups enable sequential chemical transformations necessary for constructing complex carbohydrate frameworks (Carbohydrate Research). In medicinal chemistry, (2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl triacetate functions as a building block for creating antiviral and anticancer agents, leveraging its structural similarity to natural nucleosides to enable selective targeting of viral and cancer cell polymerases (Journal of Medicinal Chemistry). Additionally, the compound finds application in the development of fluorescent probes for bioimaging, where its thiol group allows for selective labeling of biological targets such as proteins and nucleic acids (Analytical Chemistry). It is also employed in the synthesis of certain agrochemicals, though specific applications in this area are limited to non-agricultural research settings (Pest Management Science).
Reviews
Write Your Own Review