Stereoselective synthesis of oligo-α(2,8)-3-deoxy-D-manno-2- octulosonic acid derivatives

Hiroshi Tanaka; Daisuke Takahashi; Takashi Takahashi

doi:10.1002/anie.200503299

Stereoselective synthesis of oligo-α(2,8)-3-deoxy-D-manno-2- octulosonic acid derivatives

Hiroshi Tanaka, Daisuke Takahashi, Takashi Takahashi

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	770-773
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	5
DOIs	https://doi.org/10.1002/anie.200503299
Publication status	Published - 2006 Jan 23
Externally published	Yes

Keywords

Carbohydrates
Glycosides
Glycosylation
Oligosaccharides
Synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200503299

Cite this

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abstract = "(Chemical Equation Presented) 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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author = "Hiroshi Tanaka and Daisuke Takahashi and Takashi Takahashi",

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T1 - Stereoselective synthesis of oligo-α(2,8)-3-deoxy-D-manno-2- octulosonic acid derivatives

AU - Tanaka, Hiroshi

AU - Takahashi, Daisuke

AU - Takahashi, Takashi

PY - 2006/1/23

Y1 - 2006/1/23

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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.

KW - Carbohydrates

KW - Glycosides

KW - Glycosylation

KW - Oligosaccharides

KW - Synthetic methods

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Stereoselective synthesis of oligo-α(2,8)-3-deoxy-D-manno-2- octulosonic acid derivatives

Abstract

Keywords

ASJC Scopus subject areas

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