Dithiasuccinoyl (Dts) Amino-protecting Group used in Syntheses of 1,2-trans-Amino Sugar Glycosides

DOI: 10.1039/P19950000405

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 405 - 416 (1995)

Update date:2022-07-29

Topics:

Authors:

Meinjohanns, Ernst

Meldal, Morten

Paulsen, Hans

Bock, Klaus

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19950000405

Suitable protected D-glucosamine derivatives possessing the N-dithiasuccinoyl (N-Dts) protecting group of the amino function have been applied in a new alternative route to 1,2-trans-glycosylation.The O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinoylamino-β-D-glucopyranosyl) trichloroacetimidate 7 has been used to prepare corresponding β-glycosides in good yields promoted by Lewis acids.The N-dithiasuccinoyl protecting group was easy to remove by thiolysis using 2-sulfanylethanol or dithiothreitol or reductively using sodium boranuide, thus affording, after N-acetylation, the corresponding N-acetyl-β-D-glucosamine glycosides.It has been demonstrated that it is possible to reduce the Dts group in the presence of an azido group selectively by sodium boranuide or the Dts- and the azido group simultaneously by dithiothreitol, using diisopropylethylamine as a catalyst.The syntheses of the building blocks, N^α-Fmoc-Ser(Ac3-β-D-GlcNDts)-O-Pfp 10 and N^α-Fmoc-Thr(Ac3-β-D-GlcNDts)-OPfp 11, suitable for the solid-phase glycopeptide synthesis of β-O linked GlcNAc bearing glycopeptides are described.Furthermore, the preparation of the N^α-Fmoc-Asn4)-Ac2-β-D-GlcNAc>-OPfp building block 19, suitable for the solid-phase synthesis of N-glycopeptides, and the synthesis of the β-D-GlcNAc(1->6)-D-GalNAc disaccharide 27, a mucin core structure, demonstrate the use of N-dithiasuccinoyl protection in oligosaccharide synthesis.

Full text of DOI:10.1039/P19950000405

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide

Cas No:162894-87-3

R&D Labs maybe for 162894-87-3

Acorn PharmaTech Co., Ltd

Contact:86-25-58619180

Address:Nanjing High-Tech Zone 10 Xinghuo Road Pukou District Nanjing, Jiangsu 210061 The People's Republic of China
Jinan Hongfangde Pharmatech Co.LTD

Contact:0531-88870908

Address:F Bldg,750#,Shunhua Rd,New&High-tech Zone,Jinan,Shandong,China 250101
Hybio Pharmaceutica Co.,Ltd

website:http://www.hybio.com.cn

Contact:+86 755 26588093

Address:No.9 Linkong West Street, Hengdian Street, Huangpi District, Wuhan City, China.
WUXI HONOR SHINE CHEMICAL CO.,LTD

Contact:+86-510-83593312

Address:No.1699 Huishan avenue,Huishan district,Wuxi ,Jiangsu,China,214177.(Wuxi Huishan Ecomonic Develop Zone )
Jiangsu Jiuri Chemical Co.,Ltd.

Contact:+86-519-82118868

Address:Tianwang Town, Jurong City, Jiangsu Province, China

Relevant to this article

An expeditious synthesis of structural analogs of the marine cytotoxic agents grossularines-1 and -2

Doi:10.1016/0040-4039(95)00323-5
(1995)
Synthesis and biological evaluation of novel urea-and guanidine-based derivatives for the treatment of obesity-related hepatic steatosis

Doi:10.3390/molecules19056163
(2014)
Synthesis of dibenzothiophenes by pd-catalyzed dual C-H activation from diaryl sulfides

Doi:10.1002/chem.201402265
(2014)
Efficient synthesis of chiral α,β-epoxyesters via a cyclic sulfate intermediate

Doi:10.1016/S0040-4039(98)00190-7
(1998)
Synthesis of new (Pyrazol-3-yl)-1,3,4-oxadiazole derivatives by unexpected aromatization during oxidative cyclization of 4,5-dihydro-1h-pyrazole-3- carbohydrazones and their biological activities

Doi:10.1002/jhet.1765
(2014)
A New, One-Pot, Multicomponent Synthesis of Bioactive N -Pyrazolylformamidines under Microwave Irradiation

Doi:10.1055/s-0035-1561616
(2016)

Article Doi