Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations

Ryan J. Beattie; Tom Hornsby; Gemma Craig; M. Carmen Galan; Christine L. Willis

doi:10.1039/c5sc04144a

Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations

Ryan J. Beattie, Tom Hornsby, Gemma Craig, M. Carmen Galan^*, Christine L. Willis

^*Corresponding author for this work

School of Chemistry

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Abstract

A de novo approach for the rapid construction of orthogonally protected l- and d-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao-Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected l-oliose, a component of the anticancer agent aclacinomycin A.

Original language	English
Pages (from-to)	2743-2747
Number of pages	5
Journal	Chemical Science
Volume	7
Issue number	4
Early online date	11 Jan 2016
DOIs	https://doi.org/10.1039/c5sc04144a
Publication status	Published - 1 Apr 2016

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This is the final published version of the article (version of record). It first appeared online via RSC at http://pubs.rsc.org/en/Content/ArticleLanding/2016/SC/C5SC04144A#!divAbstract. Please refer to any applicable terms of use of the publisher.
Final published version, 1.75 MBLicence: CC BY

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title = "Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations",

abstract = "A de novo approach for the rapid construction of orthogonally protected l- and d-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao-Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected l-oliose, a component of the anticancer agent aclacinomycin A.",

author = "Beattie, {Ryan J.} and Tom Hornsby and Gemma Craig and Galan, {M. Carmen} and Willis, {Christine L.}",

year = "2016",

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doi = "10.1039/c5sc04144a",

language = "English",

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journal = "Chemical Science",

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AU - Beattie, Ryan J.

AU - Hornsby, Tom

AU - Craig, Gemma

AU - Galan, M. Carmen

AU - Willis, Christine L.

PY - 2016/4/1

Y1 - 2016/4/1

N2 - A de novo approach for the rapid construction of orthogonally protected l- and d-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao-Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected l-oliose, a component of the anticancer agent aclacinomycin A.

AB - A de novo approach for the rapid construction of orthogonally protected l- and d-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao-Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected l-oliose, a component of the anticancer agent aclacinomycin A.

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U2 - 10.1039/c5sc04144a

DO - 10.1039/c5sc04144a

M3 - Article (Academic Journal)

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SN - 2041-6520

VL - 7

SP - 2743

EP - 2747

JO - Chemical Science

JF - Chemical Science

IS - 4

ER -

Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations

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A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

Reworking of Novel tools for Glycoscience

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Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations

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A 13C NMR Coldprobe to Underpin Chemistry Research.

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Reworking of Novel tools for Glycoscience

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