A stereoselective synthesis of 2-acetamido-2-deoxy-C-glucosides: Glycosyl dianions as key intermediates

Matthias Hoffmann; Horst Kessler

doi:10.1016/0040-4039(94)88077-8

A stereoselective synthesis of 2-acetamido-2-deoxy-C-glucosides: Glycosyl dianions as key intermediates

Matthias Hoffmann, Horst Kessler

TUM Emeriti of Excellence

Technical University of Munich

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

49 Scopus citations

Abstract

α- Or β-C-2-acetamido-2-deoxy-C-glucosides can be obtained from the configurationally stable anomeric glycosyl dianions which are prepared by reductive lithiation (α) or transmetallation of the tin compound (β). Different electrophiles react selectively at the anomeric center.

Original language	English
Pages (from-to)	6067-6070
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	33
DOIs	https://doi.org/10.1016/0040-4039(94)88077-8
State	Published - 15 Aug 1994

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title = "A stereoselective synthesis of 2-acetamido-2-deoxy-C-glucosides: Glycosyl dianions as key intermediates",

abstract = "α- Or β-C-2-acetamido-2-deoxy-C-glucosides can be obtained from the configurationally stable anomeric glycosyl dianions which are prepared by reductive lithiation (α) or transmetallation of the tin compound (β). Different electrophiles react selectively at the anomeric center.",

author = "Matthias Hoffmann and Horst Kessler",

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T2 - Glycosyl dianions as key intermediates

AU - Hoffmann, Matthias

AU - Kessler, Horst

PY - 1994/8/15

Y1 - 1994/8/15

N2 - α- Or β-C-2-acetamido-2-deoxy-C-glucosides can be obtained from the configurationally stable anomeric glycosyl dianions which are prepared by reductive lithiation (α) or transmetallation of the tin compound (β). Different electrophiles react selectively at the anomeric center.

AB - α- Or β-C-2-acetamido-2-deoxy-C-glucosides can be obtained from the configurationally stable anomeric glycosyl dianions which are prepared by reductive lithiation (α) or transmetallation of the tin compound (β). Different electrophiles react selectively at the anomeric center.

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U2 - 10.1016/0040-4039(94)88077-8

DO - 10.1016/0040-4039(94)88077-8

M3 - Article

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

A stereoselective synthesis of 2-acetamido-2-deoxy-C-glucosides: Glycosyl dianions as key intermediates

Abstract

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