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CAS 94715-57-8

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β-D-Glucopyranose, 2-azido-2-deoxy-, 3,4,6-triacetate 1-(2,2,2-trichloroethanimidate)

Description:
β-D-Glucopyranose, 2-azido-2-deoxy-, 3,4,6-triacetate 1-(2,2,2-trichloroethanimidate) is a complex carbohydrate derivative characterized by the presence of an azido group at the 2-position of the glucopyranose ring, which is a six-membered cyclic form of glucose. The molecule features three acetyl groups at the 3, 4, and 6 positions, enhancing its solubility and reactivity. The imidate functionality at the anomeric carbon (1-position) is notable for its potential in glycosylation reactions, making it a valuable intermediate in carbohydrate chemistry. The presence of the trichloroethanimidate moiety suggests that this compound may be used in synthetic applications, particularly in the formation of glycosidic bonds. This compound is typically utilized in research settings, particularly in the synthesis of oligosaccharides and glycoconjugates. Its azido group also allows for further functionalization through click chemistry, expanding its utility in bioconjugation and material science. Overall, this compound exemplifies the intricate modifications that can be made to simple sugars to create versatile building blocks for complex molecular architectures.
Formula:C14H17Cl3N4O8
InChI:InChI=1S/C14H17Cl3N4O8/c1-5(22)25-4-8-10(26-6(2)23)11(27-7(3)24)9(20-21-19)12(28-8)29-13(18)14(15,16)17/h8-12,18H,4H2,1-3H3/t8-,9-,10-,11-,12+/m1/s1
InChI key:InChIKey=NXSDPOSAOAWHFZ-OOCWMUITSA-N
SMILES:O(C(C)=O)[C@H]1[C@H](OC(C)=O)[C@@H](COC(C)=O)O[C@@H](OC(C(Cl)(Cl)Cl)=N)[C@@H]1N=[N+]=[N-]
Synonyms:
  • β-D-Glucopyranose, 2-azido-2-deoxy-, 3,4,6-triacetate 1-(2,2,2-trichloroethanimidate)
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