Synthesis of 2′,3′-dideoxynucleosides via C-S bond cleavage: N-glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycoside

Koichi Mitsudo; Wataru Matsuda; Seiji Miyahara; Hideo Tanaka

doi:10.1016/j.tetlet.2006.05.060

Synthesis of 2′,3′-dideoxynucleosides via C-S bond cleavage: N-glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycoside

Koichi Mitsudo, Wataru Matsuda, Seiji Miyahara, Hideo Tanaka

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

8 Citations (Scopus)

Abstract

N-Glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycosides (1a) using several activators is described. NBS-promoted glycosylation reaction utilizing either the α- or β-thiodideoxyglycoside proceeded smoothly at -78 °C to give the corresponding dideoxynucleoside in a β-selective manner, presumably through a common glycosyl donor.

Original language	English
Pages (from-to)	5147-5150
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2006.05.060
Publication status	Published - Jul 17 2006

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "N-Glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycosides (1a) using several activators is described. NBS-promoted glycosylation reaction utilizing either the α- or β-thiodideoxyglycoside proceeded smoothly at -78 °C to give the corresponding dideoxynucleoside in a β-selective manner, presumably through a common glycosyl donor.",

author = "Koichi Mitsudo and Wataru Matsuda and Seiji Miyahara and Hideo Tanaka",

year = "2006",

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T1 - Synthesis of 2′,3′-dideoxynucleosides via C-S bond cleavage

T2 - N-glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycoside

AU - Mitsudo, Koichi

AU - Matsuda, Wataru

AU - Miyahara, Seiji

AU - Tanaka, Hideo

PY - 2006/7/17

Y1 - 2006/7/17

N2 - N-Glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycosides (1a) using several activators is described. NBS-promoted glycosylation reaction utilizing either the α- or β-thiodideoxyglycoside proceeded smoothly at -78 °C to give the corresponding dideoxynucleoside in a β-selective manner, presumably through a common glycosyl donor.

AB - N-Glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycosides (1a) using several activators is described. NBS-promoted glycosylation reaction utilizing either the α- or β-thiodideoxyglycoside proceeded smoothly at -78 °C to give the corresponding dideoxynucleoside in a β-selective manner, presumably through a common glycosyl donor.

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VL - 47

SP - 5147

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Synthesis of 2′,3′-dideoxynucleosides via C-S bond cleavage: N-glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycoside

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