Stereoselective Synthesis of Oligo‐α(2,8)‐3‐deoxy‐ D ‐ manno ‐2‐octulosonic Acid Derivatives | Zendy

Tanaka Hiroshi | Zendy; Takahashi Daisuke | Zendy; Takahashi Takashi | Zendy

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Stereoselective Synthesis of Oligo‐α(2,8)‐3‐deoxy‐ D ‐ manno ‐2‐octulosonic Acid Derivatives

Author(s) -

Tanaka Hiroshi,

Takahashi Daisuke,

Takahashi Takashi

Publication year - 2006

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200503299

Subject(s) - stereoselectivity , pyran , chemistry , glycal , trifluoromethanesulfonate , stereochemistry , reactivity (psychology) , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology

Iodoalkoxylation (see scheme) of a glycal with an acyclic saccharide precursor leads to an efficient stereoselective synthesis of di‐ and tri‐α(2,8)‐3‐deoxy‐ D ‐ manno ‐2‐octulosonic acid (KDO; see picture). The glycal forms α‐linked 3‐iodo‐KDO derivatives. The opening of the pyran ring improves the reactivity of the C8 hydroxy group. NIS= N ‐iodosuccimide, Tf=triflate, M.S.=molecular sieves

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