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CAS 75251-80-8

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N-boc-D-glucosamine

Description:
N-Boc-D-glucosamine is a derivative of glucosamine, characterized by the presence of a tert-butyloxycarbonyl (Boc) protecting group on the amino group. This modification enhances its stability and solubility, making it useful in various chemical applications, particularly in organic synthesis and medicinal chemistry. The compound typically appears as a white to off-white solid and is soluble in polar organic solvents. N-Boc-D-glucosamine retains the functional properties of glucosamine, which is an amino sugar involved in the synthesis of glycosaminoglycans and glycoproteins. Its structure includes a six-membered pyranose ring, an amino group, and hydroxyl groups, which contribute to its reactivity and ability to participate in glycosylation reactions. The Boc group can be removed under acidic conditions, allowing for the regeneration of the free amino group for further chemical transformations. This compound is often utilized in the synthesis of various bioactive molecules and as a building block in carbohydrate chemistry.
Formula:C11H21NO7
InChI:InChI=1/C11H21NO7/c1-11(2,3)19-10(17)12-6-8(15)7(14)5(4-13)18-9(6)16/h5-9,13-16H,4H2,1-3H3,(H,12,17)/t5-,6-,7-,8-,9?/m1/s1
SMILES:CC(C)(C)OC(=N[C@@H]1[C@H]([C@@H]([C@@H](CO)OC1O)O)O)O
Synonyms:
  • N-(tert-butoxycarbonyl)-D-glucosamine
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