3-O-(3-Nitrobenzoyl)-4,6-O-benzylidene-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-glucopyranose

 Nuclear Overhauser effect observed


3-O-(3-Nitrobenzoyl)-4,6-O-benzylidene-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-glucopyranose (8b).


 White solid, mp 108-110 ºC, Rf  (petroleum ether/EtOAc, 2:1) = 0.23,

1H NMR (500 MHz, CDCl3) 8.78 (1H, s, Ar H), 8.52-8.24 (2H, m, Ar H), 7.87 (2H, d, J 7.3 Hz, Ar H), 7.63 (1H, t, J 8.0 Hz, Ar H), 7.56-7.46 (3H, m, Ar H), 7.46-7.29 (5H, m, Ar H), 5.55 (1H, s, Ph-CH), 5.28 (1H, t, J 9.4 Hz, H-3′), 4.46 (1H, ddd, J 10.2, 8.0, 3.5 Hz, H-1′), 4.34 (1H, dd, J 10.1, 3.7 Hz, H-6′a), 4.12 (1H, q, J 7.2 Hz, H-6′b), 3.78-3.52 (3H, m, H-5′, H-4′, H-2′), 3.38 (1H, dd, J 16.7, 7.9 Hz, H-1′a), 3.04 (1H, dd, J 16.7, 3.5 Hz, H-1′b).


13C NMR (125 MHz, CDCl3) 196.6, 164.1, 147.1, 135.7, 134.6, 128.6, 128.0, 127.5, 127.2, 127.1, 126.6, 125.0, 123.7, 100.4, 77.5, 75.8, 75.6, 72.6, 69.7, 67.6, 40.1.

HRMS (ESI): calcd for C28H25NO9Na: m/z 542.1422 [M + Na]+ ; found 542.1418.


ARKIVOC Volume 2016

Selective acylation and sulfonylation of 4,6-O-benzylidene-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-glucopyranose (JY-9345IP) 
Xiaomin Gu and Zhijie Fang
Full Text: PDF (363K)
pp. 233 - 249 
received Jul 16 2015; accepted Nov 27 2015; published Dec 17 2015;
Selective acylation and sulfonylation of 4,6-O-benzylidene-1-deoxy- 1-(2-oxo-2-phenylethyl)-β-D-glucopyranose Xiaomin Gu and Zhijie Fang* School of Chemical Engineering, Nanjing University of Science & Technology, 200 Xiaolingwei St, Nanjing, JiangSu 210 094, P. R. China E-mail: zjfang@njust.edu.cn Dedicated to Jhillu Singh Yadav to mark his outstanding contributions to synthetic organic chemistry
DOI: http://dx.doi.org/10.3998/ark.5550190.p009.345 



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