Organic Letters
Letter
(9) (a) Sun, F.; Xu, G.; Wu, J.; Yang, L. Tetrahedron: Asymmetry
2007, 18, 2454. (b) Sonnet, P. E.; Gazzillo, J. A.; Dudley, R. L.;
Boswell, R. T. Chem. Phys. Lipids 1990, 54, 205.
(10) Rajakumar, P.; Murali, V. Synth. Commun. 2003, 33, 3891.
(11) Asahina, Y.; Fujimoto, R.; Suzuki, A.; Hojo, H. J. Carbohydr.
Chem. 2015, 34, 12.
In summary, we revealed that the MBn groups installed on
both primary and secondary alcohols smoothly cleave by the
use of DDQ. The oxidation is believed to be promoted by the
inductive effect of the methyl group. Additionally, the selective
removal of the PMB group in the presence of the MBn group
was achieved by the treatment of CAN. These results will
accelerate the use of the MBn group in organic synthesis and
will advance site-specific transformations in polyhydroxy
systems.
(12) Selected papers for oxidation of MBn THP ether:
(a) Khosropour, A. R.; Khodaei, M. M.; Ghaderi, S. Z. Naturforsch.,
B: J. Chem. Sci. 2006, 61b, 326. (b) Firouzabadi, H.; Hazarkhani, H.;
Hassani, H. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 403.
(c) Heravi, M. M.; Kazemian, P.; Oskooie, H. A.; Ghassemzadeh, M.
J. Chem. Res. 2005, 105. (d) Narender, M.; Reddy, M. S.; Kumar, V.
P.; Nageswar, Y. V. D.; Rao, K. R. Tetrahedron Lett. 2005, 46, 1971.
(13) Selected papers for oxidation of MBn methyl ether: (a) Song,
Z.-Z.; Gong, J.-L.; Zhang, M.; Wu, X.-F. Asian J. Org. Chem. 2012, 1,
214. (b) Shen, Z.; Dai, J.; Xiong, J.; He, X.; Mo, W.; Hu, B.; Sun, N.;
Hu, X. Adv. Synth. Catal. 2011, 353, 3031. (c) Iranpoor, N.;
Firouzabadi, H.; Pourali, A. R. Synth. Commun. 2005, 35, 1527.
(d) Strazzolini, P.; Runcio, A. Eur. J. Org. Chem. 2003, 526.
(14) Yu, B.; Jiang, T.; Li, J.; Su, Y.; Pan, X.; She, X. Org. Lett. 2009,
11, 3442.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
Experimental procedures, analytical data, and copies of
1
the H and 13C NMR spectra for all new products
(15) Selected papers for the deprotection of the PMB groups by
using a protic acid: (a) Ai, Y.; Kozytska, M. V.; Zou, Y.; Khartulyari,
A. S.; Maio, W. A.; Smith, A. B., III J. Org. Chem. 2018, 83, 6110.
(b) Guillaume, J.; Seki, T.; Decruy, T.; Venken, K.; Elewaut, D.; Tsuji,
M.; Calenbergh, S. V. Org. Biomol. Chem. 2017, 15, 2217. (c) Mondal,
S.; Sureshan, K. M. J. Org. Chem. 2016, 81, 11635. (d) Swarts, B. M.;
Guo, Z. J. Am. Chem. Soc. 2010, 132, 6648.
AUTHOR INFORMATION
Corresponding Authors
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ORCID
(16) Selected papers for the deprotection of the PMB groups by
Notes
́
using a Lewis acid: (a) Glaus, F.; Dedic, D.; Tare, P.; Nagaraja, V.;
Rodrigues, L.; Aínsa, J. A.; Kunze, J.; Schneider, G.; Hartkoorn, R. C.;
Cole, S. T.; Altmann, K.-H. J. Org. Chem. 2018, 83, 7150. (b) Yoshida,
R.; Ouchi, H.; Yoshida, A.; Asakawa, T.; Inai, M.; Egi, M.;
Hamashima, Y.; Kan, T. Org. Biomol. Chem. 2016, 14, 10783.
(c) Sawama, Y.; Masuda, M.; Asai, S.; Goto, R.; Nagata, S.;
Nishimura, S.; Monguchi, Y.; Sajiki, H. Org. Lett. 2015, 17, 434.
(d) Carr, J. L.; Offermann, D. A.; Holdom, M. D.; Dusart, P.; White,
A. J. P.; Beavil, A. J.; Leatherbarrow, R. J.; Lindell, S. D.; Sutton, B. J.;
Spivey, A. C. Chem. Commun. 2010, 46, 1824.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
JSPS KAKENHI (Grant Nos. JP19K15549, JP18H04429, and
JP19H02727) partly supported this work.
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(17) All of the MBn group(s) in the reactants as shown in Schemes
2 and 4, and Table 1 were incorporated via the Williamson ether
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1
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