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

Hiroshi Tanaka Dr.

Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: (+81) 3-5734-2884

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Daisuke Takahashi,

Daisuke Takahashi

Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: (+81) 3-5734-2884

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Takashi Takahashi Prof. Dr.,

Takashi Takahashi Prof. Dr.

[email protected]

Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: (+81) 3-5734-2884

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Hiroshi Tanaka Dr.,

Hiroshi Tanaka Dr.

Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: (+81) 3-5734-2884

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Daisuke Takahashi,

Daisuke Takahashi

Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: (+81) 3-5734-2884

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Takashi Takahashi Prof. Dr.,

Takashi Takahashi Prof. Dr.

[email protected]

Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: (+81) 3-5734-2884

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First published: 17 January 2006

https://doi.org/10.1002/anie.200503299

Citations: 42

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Graphical Abstract

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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References

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Volume45, Issue5

January 23, 2006

Pages 770-773

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

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

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