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Glycoscience pp 451–524Cite as

Glycosyl Trichloroacetimidates

  • Reference work entry

Abstract

In the first part of this review, the basic principles of chemical glycosylation reactions are discussed; this way the advantages of O‑glycosyl trichloroacetimidates and related systems as glycosyl donors become obvious. Many new methods for the generation of O‑glycosyl trichloroacetimidates and for their use as glycosyl donors have been introduced which are compiled as well as their use in solid-phase oligosaccharide synthesis. The power of these glycosyl donors is demonstrated by their application in complex oligosaccharide and glycoconjugate synthesis, as outlined in the second part of this review. Recent applications in glycolipid, glycosyl amino acid and glycopeptide, nucleoside and nucleotide glycosidation, glycosamino glycan, cell wall constituent, and GPI anchor synthesis, glycosylation of various natural products and their metabolites, and finally cyclooligosaccharide generation are compiled. In the last section, related glycosyl donors are briefly discussed.

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Abbreviations

ADMB:

4‑acetoxy-2,2‑dimethylbutanoyl

CAc:

chloroacetyl

CDs:

cyclodextrins

CSs:

chondroitin sulfates

DBU:

1,8‑diazabicyclo[5.4.0]undec-7-ene

DDQ:

2,3-dichloro-5,6-dicyno-benzoquinone

DMM:

N‑dimethylmaleoyl

DPM:

diphenylmethyl

FGFs:

fibroblast growth factors

Fmoc:

9‑fluorenylmethyl carbamate

GAGs:

glycosaminoglycans

GPI:

glycosylphosphatidyl inositol

HS:

heparan sulfate

ILs:

ionic liquids

IP:

inverse procedure

IPG:

inositolphosphoglycan

LTAs:

lipoteichoic acids

MPEG:

mono-methyl polyethyleneglycol

MPLC:

medium pressure liquid chromatography

NAP:

naphthylmethyl

PLL:

photolabile linker

PNBP:

p-nitrobenzylpyridine

PPTS:

pyridinium p-toluenesulfonate

PTBD:

polymer‐supported 1,5,7‑triazabicyclo[4.4.0]dec-5-ene

PS-DBU:

polystyrene‐supported DBU

SPOS:

solid-phase oligosaccharide syntheses

TBS:

tert-butyl-dimethylsilyl

TMSOTf:

trimethylsilyl trifluoromethanesulfonate

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Acknowledgement

Our work reported in this chapter was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

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Authors and Affiliations

  1. Fachbereich Chemie, Fach M 725, Universität Konstanz, 78457, Konstanz, Germany

    Richard R. Schmidt

  2. School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland

    Xiangming Zhu

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Correspondence to Richard R. Schmidt .

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Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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Schmidt, R.R., Zhu, X. (2008). Glycosyl Trichloroacetimidates. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_11

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