Volume 20, Issue 22
Natural Products
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ChemInform Abstract: Practical Synthesis of Deoxymannojirimycin and of (2S,3R,4R,5R)-3,4,5-Trihydroxypipecolic Acid from D-Glucose.

G. W. J. FLEET

G. W. J. FLEET

Dyson Perrins Lab., Oxford Cent. Mol. Sci., Oxford Univ., Oxford OX1 3QY, UK

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N. G. RAMSDEN

N. G. RAMSDEN

Dyson Perrins Lab., Oxford Cent. Mol. Sci., Oxford Univ., Oxford OX1 3QY, UK

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D. R. WITTY

D. R. WITTY

Dyson Perrins Lab., Oxford Cent. Mol. Sci., Oxford Univ., Oxford OX1 3QY, UK

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First published: May 30, 1989

Abstract

Deoxymannojirimycin (X) is synthesized as shown in the scheme starting from the glucose derivative (II) which is readily available from diacetone glucose (I).

ChemInform Abstract

Deoxymannojirimycin (X) is synthesized as shown in the scheme starting from the glucose derivative (II) which is readily available from diacetone glucose (I). The overall yield of (X) from (I) amounts to 35%. In addition, the intermediate lactol (VIII) can be converted to the trihydroxypipecolic acid (XI).

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