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CAS 18031-51-1

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α-D-Glucopyranoside, methyl, 2,3,6-triacetate

Description:
α-D-Glucopyranoside, methyl, 2,3,6-triacetate is a derivative of glucose, specifically a methylated form of α-D-glucopyranose with three acetyl groups attached at the 2, 3, and 6 positions. This compound is characterized by its sweet taste, typical of sugar derivatives, and is often used in organic synthesis and as a building block in carbohydrate chemistry. It is a white to off-white crystalline solid that is soluble in organic solvents such as methanol and dichloromethane, but less soluble in water due to the presence of the hydrophobic acetyl groups. The acetylation enhances its stability and alters its reactivity compared to the parent sugar. In terms of applications, it may be utilized in the synthesis of glycosides, as well as in studies related to glycoproteins and polysaccharides. Its chemical structure allows for various functional group transformations, making it a versatile intermediate in synthetic organic chemistry. Safety data should be consulted for handling and storage, as with all chemical substances.
Formula:C13H20O9
InChI:InChI=1S/C13H20O9/c1-6(14)19-5-9-10(17)11(20-7(2)15)12(21-8(3)16)13(18-4)22-9/h9-13,17H,5H2,1-4H3/t9-,10-,11+,12-,13+/m1/s1
InChI key:InChIKey=SZWIADUEFWYSBL-LBELIVKGSA-N
SMILES:O(C(C)=O)[C@@H]1[C@@H](OC(C)=O)[C@H](O)[C@@H](COC(C)=O)O[C@@H]1OC
Synonyms:
  • Methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside
  • Glucopyranoside, methyl, 2,3,6-triacetate, α-D-
  • α-D-Glucopyranoside, methyl, 2,3,6-triacetate
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