CAS 136656-49-0

3,4-di-O-acetyl-6-O-(tert-butyldimethyl-silyl)-D-

Description:

3,4-di-O-acetyl-6-O-(tert-butyldimethyl-silyl)-D-glucopyranose, identified by CAS number 136656-49-0, is a derivative of D-glucose that features specific protective groups. The presence of two acetyl groups at the 3 and 4 positions and a tert-butyldimethylsilyl (TBDMS) group at the 6 position indicates that this compound is designed for use in organic synthesis, particularly in glycosylation reactions. The acetyl groups serve to protect the hydroxyl groups from unwanted reactions, while the TBDMS group provides stability and solubility in organic solvents, facilitating further chemical transformations. This compound is typically used in carbohydrate chemistry, especially in the synthesis of oligosaccharides and glycosides. Its structural modifications enhance its reactivity and selectivity in various chemical reactions, making it a valuable intermediate in the synthesis of more complex carbohydrate structures. As with many silyl-protected compounds, it can be deprotected under specific conditions to yield the corresponding hydroxyl-functionalized sugar.

Formula: C₁₆H₂₈O₆Si

InChI: InChI=1/C16H28O6Si/c1-11(17)21-13-8-9-19-14(15(13)22-12(2)18)10-20-23(6,7)16(3,4)5/h8-9,13-15H,10H2,1-7H3/t13-,14-,15-/m1/s1

SMILES: CC(=O)O[C@@H]1C=CO[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H]1OC(=O)C

Synonyms:

• 3,4-Di-O-acetyl-6-O-(tert-butyldimethylsilyl)-D-galactal
• 3,4-di-O-acetyl-2,6-anhydro-1-O-[tert-butyl(dimethyl)silyl]-5-deoxy-D-arabino-hex-5-enitol