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Amino and hydroxy acid based diastereoselective synthesis of 1-deoxygalactostatin and its imino acid derivative

✍ Scribed by María Ruiz; Tania M. Ruanova; Vicente Ojea; JoséM. Quintela

Book ID
104260905
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
260 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

l-Deoxygalactostatin (2) and (2S, 3S, 4R, 5S)-trihydroxypipecolic acid (15) have been synthesised from known building blocks derived from glycine, D-valine and L-tartaric acid (eight and seven steps, with 23% and 27% yield, respectively), via a syn-aldol reaction between 4-O-(tertbutyldiphenylsilyl)-2,3-O-isopropylidene-L-threose (6) and the stannous salt of the Sch611kopf's bislactim ether 7b.

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