Synthesis of Azidosphingosine from D-Galactose or L-Arabinose
- Corresponding author: Gao Yangguang, sunlt413@jhun.edu.cn
Citation:
Gao Yangguang, Cao Zhou, Han Zhongxiang, Zhang Qiang, Hu Jie, Guo Rui, He Xianran, Ding Fei, You Qingliang, Zhang Yongmin. Synthesis of Azidosphingosine from D-Galactose or L-Arabinose[J]. Chinese Journal of Organic Chemistry,
;2019, 39(2): 390-396.
doi:
10.6023/cjoc201808044
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Reagents and conditions: (a) PhCH(OMe)2, PTSA, DMF (dry), 85%; (b) NaIO4, MeOH, H2O; (c) CH3Ph3P+·Br-, n-BuLi, THF, 81% for 2 steps; (d) 1-pentadecene (3a), Grubbs Ⅱ catalyst, 62% for 4a, 10% for 4b; (e) p-toluenethiol, AIBN, toluene, reflux, 64%; (f) Ph3P, DEAD, DPPA, THF (dry), 72%; (g) (ⅰ) Tf2O, DCM, pyridine (dry), -20 ˚C to r.t.; (ⅱ) NaN3, DMF (dry), 45% for 5, 38% for 6; (h) (ⅰ) MsCl, DCM, Et3N, -30 ˚C to r.t.; (ⅱ) NaN3, DMF, 90 ˚C, 40%; (ⅰ) 1% AcCl in methanolic solution, 89%.
Reagents and conditions: (a) (ⅰ) PTSA, MeOH; (ⅱ) PhCH(OMe)2, CH3CN, 85% yield for 2 steps; (b) 1-pentadecene, Grubbs Ⅱ catalyst, 65% yield for 10, 90% yield for 13; (c) Ⅰ2, PPh3, imidazole, THF, 91% yield; (d) NaN3, DMF, 50 ℃, 75% yield for 7; (e) PTSA, MeOH, 82% yield.