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CAS 187269-63-2

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α-D-Mannopyranosyl fluoride, 2,3,4,6-tetrakis(2,2-dimethylpropanoate)

Description:
α-D-Mannopyranosyl fluoride, 2,3,4,6-tetrakis(2,2-dimethylpropanoate) is a glycosyl fluoride derivative of mannose, characterized by its pyranose ring structure. This compound features a fluorine atom at the anomeric carbon (C1) of the mannose sugar, which enhances its reactivity in glycosylation reactions, making it a valuable intermediate in carbohydrate chemistry. The presence of four 2,2-dimethylpropanoate ester groups at the C2, C3, C4, and C6 positions contributes to its solubility and stability, as well as its potential applications in synthetic organic chemistry. The bulky ester groups can also influence the compound's steric properties and reactivity. This compound is typically used in research settings, particularly in the synthesis of oligosaccharides and glycoproteins, due to its ability to participate in selective glycosylation reactions. As with many glycosyl fluorides, it is important to handle this substance with care, as it may be reactive and sensitive to moisture.
Formula:C26H43FO9
InChI:InChI=1S/C26H43FO9/c1-23(2,3)19(28)32-13-14-15(34-20(29)24(4,5)6)16(35-21(30)25(7,8)9)17(18(27)33-14)36-22(31)26(10,11)12/h14-18H,13H2,1-12H3/t14-,15-,16+,17+,18+/m1/s1
InChI key:InChIKey=YGQXZOVKBRJLJC-ZBRFXRBCSA-N
SMILES:O(C(C(C)(C)C)=O)[C@H]1[C@H](OC(C(C)(C)C)=O)[C@H](OC(C(C)(C)C)=O)[C@@H](F)O[C@@H]1COC(C(C)(C)C)=O
Synonyms:
  • α-D-Mannopyranosyl fluoride, 2,3,4,6-tetrakis(2,2-dimethylpropanoate)
  • Tetra-O-pivaloyl-α-D-mannosyl fluoride
  • α-D-Mannopyranosyl fluoride, tetrakis(2,2-dimethylpropanoate)
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