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Synthesis of 4-deacetyl-1-dimethylsilyl-7-triethylsilylbaccatin III.

The Journal of organic chemistry (2009-02-10)
Mark E Ondari, Kevin D Walker
ABSTRACT

A one-pot trisilylation step to protect three hydroxyl groups of baccatin III (1), followed by hydride ester cleavage and base hydrolysis of a triethylsilyl ether at C13, provides efficient access to a key intermediate 9 (top path). This route removes two steps from a previously established reaction sequence to 9 (bottom path). In principle, inclusion of the truncated reaction sequence into widely utilized semisynthetic routes to next generation Taxol (paclitaxel) compounds could conceivably shorten the overall process.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Baccatin III, ≥95% (HPLC)