Treatment of methyl b-D-glucopyranoside, methyl a-D-glucopyranoside, 2-azido-2-deoxy-b-D-galactopyranosyl fluoride, and 1,6-anhydro-b-lactose with di-t-butyldichlorosilane gave the corresponding 4,6-cyclic di-t-butylsilylenediyl ether (4,6-CDBS) derivatives in high yields. It was suggested that the
The di-t-butylsilylene protecting group for diols
โ Scribed by Barry M. Trost; Charles G. Caldwell
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 217 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Di-t-butyldichlorosilane reacts with diols to yield the corresponding ai-J-butylsilylene derivatives. This useful protecting group is readily removed by treatment with pyridinium hydrofluoride.
In conjunction with our synthetic efforts directed toward pillaromycinone (I), we required a diol protecting group having the following properties: 1) stability to Lewis acids, 2) ability to be removed chemoselectively
๐ SIMILAR VOLUMES
A disadvantage in the use of the t-butyloxycarbonyl(BOC) groupls2 for N-protection in peptide synthesis is that the acidic conditions normally employed for its removal 3\*495 also effect the cleavage of the t-butyl ester group. The latter is used mainly to