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CAS 10227-18-6

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5-Thio-α-D-glucopyranose 1,2,3,4,6-pentaacetate

Description:
5-Thio-α-D-glucopyranose 1,2,3,4,6-pentaacetate is a thio derivative of α-D-glucopyranose, characterized by the presence of a thiol group (-SH) at the 5-position and five acetyl groups (-COCH3) esterified at the hydroxyl positions (1, 2, 3, 4, and 6). This compound is typically a white to off-white solid and is soluble in organic solvents such as methanol and acetone, but may have limited solubility in water due to the hydrophobic nature of the acetyl groups. The presence of the thiol group imparts unique reactivity, making it useful in various chemical reactions, including nucleophilic substitutions and as a potential ligand in coordination chemistry. Its acetylation enhances stability and can influence its biological activity, making it of interest in medicinal chemistry and carbohydrate chemistry. The compound's structure allows for potential applications in drug design, particularly in targeting specific biological pathways or as a precursor for further chemical modifications.
Formula:C16H22O10S
InChI:InChI=1S/C16H22O10S/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16+/m1/s1
InChI key:InChIKey=RFPPVTQRDZKNPS-LJIZCISZSA-N
SMILES:O(C(C)=O)[C@H]1[C@H](OC(C)=O)[C@@H](COC(C)=O)S[C@H](OC(C)=O)[C@@H]1OC(C)=O
Synonyms:
  • 5-Thio-α-D-glucopyranose 1,2,3,4,6-pentaacetate
  • Glucopyranose, 5-thio-, pentaacetate, α-D-
  • α-D-Glucopyranose, 5-thio-, pentaacetate
  • α-D-Glucopyranose, 5-thio-, 1,2,3,4,6-pentaacetate
  • 2H-Thiopyran, α-D-glucopyranose deriv.
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