Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH4

Yang-Fan Guo; Tao Luo; Guang-Jing Feng; Chun-Yang Liu; Hai Dong

doi:10.3390/molecules27185980

Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH₄

Molecules. 2022 Sep 14;27(18):5980. doi: 10.3390/molecules27185980.

Authors

Yang-Fan Guo¹, Tao Luo¹, Guang-Jing Feng¹, Chun-Yang Liu¹, Hai Dong¹

Affiliation

¹ Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry & Chemical Engineering, Huazhong University of Science & Technology, Luoyu Road 1037, Wuhan 430074, China.

Abstract

An improved method to efficiently synthesize 2-OH thioaryl glycosides starting from corresponding per-protected glycals was developed, where 1,2-anhydro sugars were prepared by the oxidation of glycals with oxone, followed by reaction of crude crystalline 1,2-anhydro sugars with NaBH₄ and aryl disulfides. This method has been further used in a one-pot reaction to synthesize glycosyl donors having both "armed" and "NGP (neighboring group participation)" effects.

Keywords: 2-OH thioglycosides; glycals; glycosyl donors; glycosylation; one-pot reaction.

MeSH terms

Disulfides
Glycosides / chemistry
Glycosylation
Sugars
Thioglycosides* / chemistry

Substances

Disulfides
Glycosides
Sugars
Thioglycosides

Grants and funding

This research was founded by the National Nature Science Foundation of China (Nos. 21772049).