An expeditious synthesis of a (3S,4S,5R)-trihydroxyazepane
โ Scribed by Dilip D. Dhavale; Vinod D. Chaudhari; Jayant N. Tilekar
- Book ID
- 104254408
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 101 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A practical approach for the synthesis of the (2S,3S,4R)-trihydroxyazepane 1d has been reported. Starting from a-D-xylo-pentodialdose, readily available from D-glucose, the sequence involves Wittig olefination and reductive amination as key steps.
๐ SIMILAR VOLUMES
The title synthesis could be accomplished by employing highly stereoselective aldol reaction of Omethyl-0-trimethylsilyl ketene acetal with the (S)-a-amido aldehyde (2) in the presence of titanium (IV) chloride as a key step.
A catalytic deuteration of protected 3,4-dehydro-L-proline using RuCI2(PPh3) 3 followed by RuO~-oxidation gave a 3,4-dideuterated L-pyroglutamic acid derivative which is considered to be a promising precursor for various deuterated amino acids. The present study demonstrates a stereoselective reduct