Citation: Yong-Kui FENG, Hua-Lan SU, Billy Joel MUKULA OTUKOL, Joel Billy, Xue-Qing ZHANG, Hui YAO, Nian-Yu HUANG. Synthesis and Crystal Structure of tert-Butyl(((2R, 3R, 6R)-3-hydroxy-6-(nitromethyl)-3, 6-dihydro-2H-pyran-2-yl)methyl)carbonate[J]. Chinese Journal of Structural Chemistry, ;2021, 40(9): 1205-1212. doi: 10.14102/j.cnki.0254–5861.2011–3120 shu

Synthesis and Crystal Structure of tert-Butyl(((2R, 3R, 6R)-3-hydroxy-6-(nitromethyl)-3, 6-dihydro-2H-pyran-2-yl)methyl)carbonate

Hubei Key Laboratory of Natural Products Research and Development, Key Laboratory of Functional Yeast (China National Light Industry), College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, China

Corresponding author: Hui YAO, yaohui@ctgu.edu.cn Nian-Yu HUANG, huangny@ctgu.edu.cn
Received Date: 26 January 2021
Accepted Date: 23 February 2021

Fund Project: the National Natural Science Foundation of China 82003621

Figures(4)

In this paper, a β-C-pyranogalactoside (IX) was synthesized from D-galactose through a nine-step reaction with a total yield of 32% under the palladium catalyst, and its structure was characterized by nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). The absolute configuration of this pyranogalactoside was confirmed with a Flack parameter of –0.01(6) by X-ray crystallography using a Cu radiation source. Compound (IX), C₁₂H₁₉NO₇, crystal data: monoclinic system, space group P2₁2₁2₁, a = 8.53480(10), b = 9.4207(2), c = 18.1308(3) Å, V = 1457.79(4) Å³, Z = 4, F(000) = 616, D_c = 1.318 g/cm³, μ = 0.931 mm⁻¹, R = 0.0294 and wR = 0.0752 for 2875 independent reflections (R_int = 0.0163) and 2857 observed ones (I > 2σ(I)).
- X-ray diffraction,
- crystal structure,
- absolute configuration,
- β-C-pyranogalactoside,
- α-glucosidase inhibitory activity
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