Synthesis and Deprotection of Cyclic Oxalate

Yun-Young Kim

doi:10.14233/ajchem.2014.16373

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Deprotection of Cyclic Oxalate

https://doi.org/10.14233/ajchem.2014.16373

Yun-Young Kim

Department of Chemistry, Dong-A University, 37 Nakdong-Daero 550 beon-gil, Saha-gu, Busan 604-714, Republic of Korea

Corresponding Author(s) : Yun-Young Kim

yoyoyokim@hanmail.net

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 18, 2014

Abstract

As a new protective group for diols, cyclic oxalates [trans-1,2-cyclo-hexane diol 1,2-oxalate (1), 1,2:5,6-di-O-isopropylidene-D-mannitol 3,4-oxalate (2) and 1,2-propanediol 1,2-oxalate (3)] were synthesized by using oxalyl chloride, ethyloxalyl chloride, diethyl oxalate and oxalic acid. Cyclic oxalates were readily cleaved to the corresponding diols by various bases such as sodium methoxide, potassium carbonate, 1 % sodium hydroxide, triethylamine and lithium aluminium hydride, but were stable in acid.

Keywords

Cyclic oxalate Polyhydroxy compound Protection deprotection Protective group

Kim, Y.-Y. (2014). Synthesis and Deprotection of Cyclic Oxalate. Asian Journal of Chemistry, 26(19), 6364–6366. https://doi.org/10.14233/ajchem.2014.16373

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References

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References

T.W. Green, Protective Groups in Organic Synthesis, John Wiley & Sons Inc., New York, pp. 1-4 (1981).

L.D. Kohn and H.R. Kaback, J. Biol. Chem., 248, 7012 (1973).

A. Merz, Angew. Chem. Int. Ed. Engl., 12, 846 (1973); doi:10.1002/anie.197308461.

A.F. Kluge, K.G. Untch and J.H. Fried, J. Am. Chem. Soc., 94, 7827 (1972); doi:10.1021/ja00777a027.

E.J. Corey, J.-L. Gras and P. Ulrich, Tetrahedron Lett., 17, 809 (1976); doi:10.1016/S0040-4039(00)92890-9.

K.F. Bernady, M.B. Floyd, J.F. Poletto and M.J. Weiss, J. Org. Chem., 44, 1438 (1979); doi:10.1021/jo01323a017.

L. Lapatsanis, Tetrahedron Lett., 19, 3943 (1978); doi:10.1016/S0040-4039(01)95105-6.

H. Sommer and F. Cramer, Chem. Ber., 107, 24 (1974); doi:10.1002/cber.19741070104.

B.E. Cooper, Chem. Ind. (London), 794 (1978).

D.J. Ager and I. Fleming, J. Chem. Res. Synop., 6 (1977).

H. Nakai, N. Hamanaka, J. Miyake and M. Hayashi, Chem. Lett., 1499 (1979); doi:10.1246/cl.1979.1499.

E.S. Werstiuk and T. Neilson, Can. J. Chem., 50, 1283 (1972); doi:10.1139/v72-201.

I. Watanabe, T. Tsuchiya, T. Takase, S. Umezawa and H. Umezawa, Bull. Chem. Soc. Jpn., 50, 2369 (1977); doi:10.1246/bcsj.50.2369.

A.I. Meyers, K. Tomioka, D.M. Roland and D. Comins, Tetrahedron Lett., 19, 1375 (1978); doi:10.1016/S0040-4039(01)94549-6.

E.J. Corey and J.W. Suggs, J. Org. Chem., 38, 3223 (1973); doi:10.1021/jo00958a031.

K.I. Agarwal and H.G. Khorana, J. Am. Chem. Soc., 94, 3578 (1972); doi:10.1021/ja00765a054.

A.A. Nagel and L.A. Vincent, J. Org. Chem., 44, 2050 (1979); doi:10.1021/jo01326a043.

Y. Kamaya and T. Higuchi, FEMS Microbiol. Lett., 24, 225 (1984); doi:10.1111/j.1574-6968.1984.tb01309.x.

Z. Moussa and D. Romo, Synlett, 3294 (2006); doi:10.1055/s-2006-951530.

J. Romanski, P. Nowak, K. Kosinski and J. Jurczak, Tetrahedron Lett., 53, 5287 (2012); doi:10.1016/j.tetlet.2012.07.094.

J. Clayden, N. Greeves and S. Warren, Organic Chemistry, edn 2, pp. 1264 (2012).

W.C. Chan and P.D. White, Fmoc Solid Phase Peptide Synthesis, Oxford University press (2004).

W.C. Chan and P.D. White, Fmoc Solid Phase Peptide Synthesis: A Practical Approach, Oxford University Press, pp. 10-12 (2000).

R.B. Merrifield, G. Barany, W.L. Cosand, M. Engelhard and S. Mojsov, Proc. Am. Pept. Symp. 5th (1977).

A. Blanc and C.G. Bochet, Org. Lett., 9, 2649 (2007); doi:10.1021/ol070820h.

P.S. Baran, T.J. Maimone and J.M. Richter, Nature, 446, 404 (2007); doi:10.1038/nature05569.

H. Muratake, H. Kumagami and M. Natsume, Tetrahedron, 46, 6351 (1990); doi:10.1016/S0040-4020(01)96007-7.

H. Muratake and M. Natsume, Tetrahedron, 46, 6331 (1990); doi:10.1016/S0040-4020(01)96005-3.

H. Muratake and M. Natsume, Tetrahedron, 46, 6343 (1990); doi:10.1016/S0040-4020(01)96006-5.

J.A. Riddick and W.B. Bunger, Organic Solvents, edn. 5, Wiley-Interscience, New York (1970).

F.A. Carey and R.J. Sundberg, Advanced Organic Chemistry, Springer, Part 2, edn 5, pp. 433-437 (2008).

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Synthesis and Deprotection of Cyclic Oxalate

Corresponding Author(s) : Yun-Young Kim

Abstract

Keywords

Full Article

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