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Glycosyl Sulfoxides in Glycosylation Reactions

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Abstract

Carbohydrate chemistry has benefited a lot from the intrinsic reactivity of sulfoxide since it was introduced in glycosylation reactions by Kahne in 1989. Since then, extensive studies have been explored by employing sulfoxide as glycosyl donors and activation reagents in construction of glycosidic bonds. As glycosyl donors, the sulfinyl groups could locate either directly or remotely at anomeric position. This chapter focuses on the establishment and development of sulfoxides as glycosyl donors in glycosylation reactions, with an emphasis on their applications and postulated mechanisms.

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Abbreviations

ADMB:

4-allyl-1,2-dimethoxybenzene

CB:

Carboxybenzyl

CIPs:

Contact ion pairs

DDQ:

2,3-dicyano-5,6-dichlorobenzoquinone

DIPEA:

N,N-diisopropylethylamine

DMAP:

4-dimethylaminopyridine

DMDO:

Dimethyldioxirane

DTBMP:

2,6-di-tert-butyl-4-methylpyridine

E:

Electrophile

Fmoc:

9-Fluorenylmethyl

IAD:

Intramolecular aglycon delivery

LAH:

Lithium aluminum hydride

mCPBA:

3-chloroperbenzoic acid

MOM:

Methoxymethyl

Nap:

Naphthyl

NMP:

N-methyl-2-pyrrolidone

Nu:

Nucleophile

Piv:

Pivaloyl

PMB:

p-methoxybenzyl

PSB:

2-[(propan-2-yl)sulfinyl]benzyl

PTB:

2-[(propan-2-yl)thio]benzyl

SSIPs:

Solven-separated ion pairs

TBDPS:

tert-Butyldiphenylsilyl

TBS:

t-butyldimethylsilyl

TCP:

N-tetrachlorophthalimido

Tf2O:

Trifluoromethanesulfonic anhydride

TFAP:

3-trifluoroacetamidopropyl

TfOH:

Trifluoromethanesulfonic acid

TMP:

1,3,5-trimethoxybenzene

TMSE:

2-(trimethylsilyl)ethyl

TMSOTf:

Trimethylsilyl trifluoromethanesulfonate

TTBP:

2,4,5-tri-tert-butylpyrimidine

β-hFSH:

β-domain of human follicle-stimulating hormone

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Acknowledgements

We thank the National Natural Science Foundation of China (21672077, 21772050, 21472054, 21702068), the State Key Laboratory of Bioorganic and Natural Products Chemistry (SKLBNPC13425), Natural Science Funds of Hubei Province for Distinguished Young Scholars (2015CFA035), Wuhan Creative Talent Development Fund, “Thousand Talents Program” Young Investigator Award, and Huazhong University of Science and Technology for support.

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Authors and Affiliations

  1. School of Pharmacy, Huazhong University of Science and Technology, 430030, Wuhan, China

    Jing Zeng, Yan Liu, Wei Chen, Xiang Zhao, Lingkui Meng & Qian Wan

  2. Institute of Brain Research, Huazhong University of Science and Technology, 430030, Wuhan, Hubei, China

    Jing Zeng, Yan Liu, Wei Chen, Xiang Zhao, Lingkui Meng & Qian Wan

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  1. Jing Zeng
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  2. Yan Liu
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  3. Wei Chen
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  4. Xiang Zhao
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Correspondence to Qian Wan.

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This article is part of the Topical Collection “Sulfur Chemistry”; edited by Xuefeng Jiang.

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Zeng, J., Liu, Y., Chen, W. et al. Glycosyl Sulfoxides in Glycosylation Reactions. Top Curr Chem (Z) 376, 27 (2018). https://doi.org/10.1007/s41061-018-0205-4

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