Effect of Anomeric Configuration on Stereocontrolled α-Glycosylation of l-Fucose

Lihao Wang; Fei Fan; Haotian Wu; Lei Gao; Ping Zhang; Tiantian Sun; Chendong Yang; Guangli Yu; Chao Cai

doi:10.1055/s-0037-1611311

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(20): 2701-2706
DOI: 10.1055/s-0037-1611311

letter

Effect of Anomeric Configuration on Stereocontrolled α-Glycosylation of l-Fucose

Lihao Wang ◊

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Fei Fan ◊

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Haotian Wu

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Lei Gao

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Ping Zhang

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Tiantian Sun

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Chendong Yang

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Guangli Yu

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^bLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, P. R. of China

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Chao Cai*

^aKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China eMail: caic@ouc.edu.cn

^bLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, P. R. of China

^cShandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

^◊ These authors contributed equally to this work

Abstract

In this letter, we report an approach to the stereoselective α-glycosylation of l-fucose that is exemplified by effect of anomeric configuration. The neighboring group participation is not compatible with α-glycosylation of l-fucose, therefore the remote participation by 4-O-Bz was employed to control the formation of 1,2-cis-glycosidic bond. Furthermore, we found the anomeric configuration of fucose donor is crucial to stereoselectivity of the glycosylated products. The α/β-mixed products were generated by using β-anomeric donor while the glycosyl donor in α configuration yielded products in high α-selectivity possibly due to the distinct pathway to forming the key intermediates. This phenomenon supplies the basis for the synthesis of complicated natural carbohydrates containing fucose α-glycoside, such as fucoidans, fucosylated N-glycans, and fucosylated chondroitin sulfates, etc.

Key words

α-l-fucoside - stereoglycosylation - thioglycoside donor - anomeric configuration - remote participation

Volltext

Referenzen

References and Notes

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25 General Procedure for Fucosylation of 4α with AcceptorsTo a solution of compound 4α (10 mg, 0.0225 mmol, 1 equiv) and acceptor (0.0248–0.225 mmol, 1.1–10 equiv) in 500 μL anhyd Et₂O with argon protection was added 4 Å MS. The mixture was stirred at room temperature for 0.5 h and then cooled to 0 °C, then NIS (10.1 mg, 0.045 mmol, 2 equiv) and TMSOTf (0.4 μL, 0.00225 mmol, 0.1 equiv) were added. The mixture was stirred for 0.5 h after which TLC indicated full conversion and quenched with Et₃N. The mixture was filtered, evaporated, and purified by column chromatography to afford product.
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28 Analytical Data for Product 23 ¹H NMR (500 MHz, CDCl₃): δ = 8.08 (d, J = 7.3 Hz, 2 H), 7.64 (t, J = 7.4 Hz, 1 H), 7.51 (t, J = 7.7 Hz, 2 H), 7.37–7.30 (m, 5 H), 5.82 (d, J = 3.6 Hz, 1 H), 5.53 (d, J = 2.6 Hz, 1 H), 5.37 (dd, J = 10.6, 3.2 Hz, 1 H), 5.01 (d, J = 3.5 Hz, 1 H), 4.75 (d, J = 12.1 Hz, 1 H), 4.60 (d, J = 5.6 Hz, 1 H), 4.56 (d, J = 12.2 Hz, 1 H), 4.41–4.36 (m, 1 H), 4.34 (d, J = 3.6 Hz, 1 H), 4.31 (d, J = 3.1 Hz, 1 H), 4.17 (dd, J = 8.6, 6.2 Hz, 1 H), 4.11 (dd, J = 9.1, 3.1 Hz, 1 H), 4.03–3.99 (m, 2 H), 1.96 (s, 3 H), 1.50 (s, 3 H), 1.42 (s, 3 H), 1.37 (s, 3 H), 1.29 (s, 3 H), 1.14 (d, J = 6.5 Hz, 3 H).¹³C NMR (126 MHz, CDCl₃): δ = 170.12, 166.05, 138.16, 133.28, 129.80, 129.72, 128.53, 128.49, 127.97, 127.68, 111.93, 109.22, 105.38, 96.00, 82.31, 81.08, 78.34, 73.80, 73.53, 72.20, 72.09, 70.43, 67.97, 65.27, 26.95, 26.87, 26.24, 25.36, 20.87, 15.88. HRMS: m/z calcd for [C₃₄H₄₂NaO₁₂]⁺: 665.2568; found: 665.2565.

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