Synthesis of D-erythro-sphingosine from D-glucosamine

DOI: 10.1248/cpb.44.927

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 927 - 932 (1996)

Update date:2022-08-02

Topics: Final steps Deacetylation Ozonolysis Protection of Amino Group

Authors:

Shinozaki, Katsuo

Mizuno, Kazuhiro

Masaki, Yukio

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Article abstract of DOI:10.1248/cpb.44.927

D-erythro-Sphingosine (1) was synthesized from D-glucosamine (2) as a chiral pool through stereoinversion of the C(3)-hydroxyl group via an oxidation-reduction sequence, transformation to the erythro-amino-alcohol chiron (9) protected as the oxazolidinone, and elongation of the side chain at the C(6)-position of the derived chloride (12).

Full text of DOI:10.1248/cpb.44.927

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