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t-Butyldimethylsilyl (TBDMS) as protective group in carbohydrate chemistry migration of the tbdms group in trans-diol systems

✍ Scribed by C. A. A. van Boeckel; S. F. van Aelst; T. Beetz


Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
157 KB
Volume
102
Category
Article
ISSN
0165-0513

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Protecting group migration in the chemis
✍ StΓ©phane GΓ©rard; Jacqueline Marchand-Brynaert πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 112 KB

The alkoxide anion derived from 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone (1) rearranged at -78Β°C into amide anion by N-O migration of the silyl protecting group. The occurrence of this intermediate was proved by quenching with benzyl bromide and phenethyl chloroformate, giving respective