Syn-selective dihydroxylation of γ-amino-α, β-unsaturated (Z)-esters from D-serine:: stereoselective synthesis of D-iminolyxitol

Jeon, Jongho; Lee, Jong Hyup; Kim, Jung-Won; Kim, Young Gyu

doi:10.1016/j.tetasy.2007.10.004

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Syn-selective dihydroxylation of γ-amino-α, β-unsaturated (Z)-esters from D-serine:: stereoselective synthesis of D-iminolyxitol

Jeon, Jongho;
Lee, Jong Hyup;
Kim, Jung-Won;
Kim, Young Gyu

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17

초록

An efficient and stereoselective synthesis of D-iminolyxitol, a potent alpha-galactosidase inhibitor, is achieved in 11 steps over 45% overall yield from N-Boc-O-Bn-D-serine. The key step involves the OsO4-catalyzed syn-selective dihydroxylation reaction of the acyclic gamma-amino-alpha,beta-unsaturated (Z)-ester controlled by an N-diphenylmethylene group. (c) 2007 Elsevier Ltd. All rights reserved.

키워드

SOLID-PHASE SYNTHESIS; ASYMMETRIC-SYNTHESIS; POLYHYDROXYLATED PYRROLIDINES; ENANTIOSPECIFIC SYNTHESIS; RIBO-PHYTOSPHINGOSINE; CALLIPELTIN-A; AZA-SUGARS; ACIDS; EFFICIENT; ANALOGS

제목: Syn-selective dihydroxylation of γ-amino-α, β-unsaturated (Z)-esters from D-serine:: stereoselective synthesis of D-iminolyxitol

저자: Jeon, Jongho; Lee, Jong Hyup; Kim, Jung-Won; Kim, Young Gyu

DOI: 10.1016/j.tetasy.2007.10.004

발행일: 2007-10-10

유형: Article

저널명: Tetrahedron Asymmetry

권: 18

호: 20

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