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CAS 81058-27-7

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α-D-Glucopyranosyl bromide, 2,3,4,6-tetrakis(2,2-dimethylpropanoate)

Description:
α-D-Glucopyranosyl bromide, 2,3,4,6-tetrakis(2,2-dimethylpropanoate) is a glycosyl bromide derivative of glucose, characterized by its glycosidic structure and the presence of bromine as a leaving group. This compound features a glucopyranose ring, which is a six-membered cyclic form of glucose, and is further modified with four ester groups derived from 2,2-dimethylpropanoic acid. These esterifications enhance the compound's lipophilicity and stability, making it useful in various synthetic applications, particularly in carbohydrate chemistry. The bromide group serves as an electrophilic site, facilitating nucleophilic substitution reactions, which are essential in the synthesis of glycosides and oligosaccharides. The compound is typically used in research settings for the development of glycosylation reactions and can serve as a building block in the synthesis of more complex carbohydrate structures. Its properties, such as solubility and reactivity, are influenced by the bulky ester groups, which can also affect its interaction with biological systems.
Formula:C26H43BrO9
InChI:InChI=1S/C26H43BrO9/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=BSDBCYHGMPHOAL-SFFUCWETSA-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](Br)O[C@@H]1COC(C(C)(C)C)=O
Synonyms:
  • 2,3,4,6-Tetra-O-Pivaloyl-Alpha-D-Glucopyranosyl Bromide
  • 2,3,4,6-Tetra-O-Pivaloyl-α-D-Glucopyranosyl  Bromide
  • 2,3,4,6-Tetra-O-pivaloyl-α-<span class="text-smallcaps">D</span>-glucopyranosyl bromide
  • 2,3,4,6-tetra-O-pivaloyl-alpha-D-glucopyranosylbromide
  • Tetra-O-pivaloyl-α-<span class="text-smallcaps">D</span>-glucopyranosyl bromide
  • α-<span class="text-smallcaps">D</span>-Glucopyranosyl bromide, 2,3,4,6-tetrakis(2,2-dimethylpropanoate)
  • α-<span class="text-smallcaps">D</span>-Glucopyranosyl bromide, tetrakis(2,2-dimethylpropanoate)
  • α-L-altropyranosyl bromide, tetrakis(2,2-dimethylpropanoate)
  • α-D-Glucopyranosyl bromide, 2,3,4,6-tetrakis(2,2-dimethylpropanoate)
  • Tetra-O-pivaloyl-α-D-glucopyranosyl bromide
  • α-D-Glucopyranosyl bromide, tetrakis(2,2-dimethylpropanoate)
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