Anhydrosugars
2.4
301
Application of the ring-closing olefin metathesis reaction (RCM) for the preparation of carbocyclic rings from the appropriately functionalized sugars is now well documented [81].
Recently it was applied for the synthesis of compound 122, which can be regarded as a (n,m)anhydrosugar [81]. The intermediate diolefin 121 was prepared in a few standard steps from
the corresponding dialdose 120 ( > Fig. 28) [82].
6 Conclusion
This chapter briefly describes different classes of anhydrosugars, both anomeric and nonanomeric. Attention is paid mostly to anhydrosugars of great importance such as 1,6- and
1,2-anhydrosugars, and non-anomeric sugar epoxides. Several anhydrosugars (mostly the
modified ones with the nucleoside structure) show interesting biological activity, the others
are used as optically pure synthons in stereocontrolled organic synthesis. The material presented in this chapter comprises the basic chemistry of such derivatives, which is already
described in many monographs and reviews (including the previous chapters from this series)
and provides new applications of such important derivatives. The new data (updating previously published work) are not comprehensive, however, they illustrate the important aspects
of the chemistry in which anhydrosugars are engaged. Therefore, only selected examples from
the new literature are included here. This material should give the reader a general impression of the chemistry of such compounds and elucidate the modern aspects of anhydrosugar
chemistry.
References
1. Jarosz S (2001) Glycoscience—Chemistry and
Chemical Biology 1:291
2. Stick RV, Williams SJ (2001) Glycoscience—
Chemistry and Chemical Biology 1:627
3. Cerny M (2003) Adv Carbohydr Chem Biochem
58:121
4. Ball DH, Parish FW (1969) Adv Carbohydr Chem
Biochem 24:139
5. Williams NR (1970) Adv Carbohydr Chem
Biochem 25:109
6. Cerny M, Stanek J Jr (1977) Adv Carbohydr
Chem Biochem 34:23
7. Ferrier RJ, Middleton S (1993) Chem Rev
93:2779
8. Hanessian S (1983) Total Synthesis of Natural
Products: The Chiron Approach. Pergamon Press,
New York; Inch TD (1984) Tetrahedron 40:3161;
Fraser-Reid B, Tsang R (1989) Strategies and
Tactics in Organic Synthesis. Academic Press,
New York
9. Mitsunobu O (1981) Synthesis 1
10. Castro BR (1983) Org React 29:1
11. Zottola MA, Alonso R, Vite GD, Fraser-Reid B
(1989) J Org Chem 54:6123
12. Bailliez V, de Figuiredo RM, Olesker A,
Cleophax J (2003) Synthesis 1015
13. Dromowicz M, Köll P (1998) Carbohydr Res
308:169
14. Wiggins LF (1963) Methods Carbohydr Chem
2:188; Whistler RL, Lake WC (1972) Methods
Carbohydr Chem 6:286
15. Lundt I, Skelbaek-Pedrsen B Acta Chim Scand
Ser B (1981) 35:637; Skelto B, Stick RV, Matthew
D (2000) Austr J Chem 53:389; Sridhar P, Saravanan V, Chandrasekarn S (2005) Pure Appl
Chem 77:145
16. Sivapriya K, Chandrasekaran S (2006) Carbohydr
Res 341:2204
17. Fuenets J, Olano D, Pradera MA Tetrahedron Lett
(1999) 40:4063
18. Krohn K, Gehle D, Flörke U (2005) Eur J Org
Chem 2841
19. Krohn K, Gehle D, Flörke U (2005) Eur J Org
Chem 4557
20. Witczak ZJ, Kaplon P, Kolodziej M (2002) J Carbohydr Chem 21:143
21. Kelly DR, Mahdi JG (2002) Tetrahedron Lett
43:511
2.4
301
Application of the ring-closing olefin metathesis reaction (RCM) for the preparation of carbocyclic rings from the appropriately functionalized sugars is now well documented [81].
Recently it was applied for the synthesis of compound 122, which can be regarded as a (n,m)anhydrosugar [81]. The intermediate diolefin 121 was prepared in a few standard steps from
the corresponding dialdose 120 ( > Fig. 28) [82].
6 Conclusion
This chapter briefly describes different classes of anhydrosugars, both anomeric and nonanomeric. Attention is paid mostly to anhydrosugars of great importance such as 1,6- and
1,2-anhydrosugars, and non-anomeric sugar epoxides. Several anhydrosugars (mostly the
modified ones with the nucleoside structure) show interesting biological activity, the others
are used as optically pure synthons in stereocontrolled organic synthesis. The material presented in this chapter comprises the basic chemistry of such derivatives, which is already
described in many monographs and reviews (including the previous chapters from this series)
and provides new applications of such important derivatives. The new data (updating previously published work) are not comprehensive, however, they illustrate the important aspects
of the chemistry in which anhydrosugars are engaged. Therefore, only selected examples from
the new literature are included here. This material should give the reader a general impression of the chemistry of such compounds and elucidate the modern aspects of anhydrosugar
chemistry.
References
1. Jarosz S (2001) Glycoscience—Chemistry and
Chemical Biology 1:291
2. Stick RV, Williams SJ (2001) Glycoscience—
Chemistry and Chemical Biology 1:627
3. Cerny M (2003) Adv Carbohydr Chem Biochem
58:121
4. Ball DH, Parish FW (1969) Adv Carbohydr Chem
Biochem 24:139
5. Williams NR (1970) Adv Carbohydr Chem
Biochem 25:109
6. Cerny M, Stanek J Jr (1977) Adv Carbohydr
Chem Biochem 34:23
7. Ferrier RJ, Middleton S (1993) Chem Rev
93:2779
8. Hanessian S (1983) Total Synthesis of Natural
Products: The Chiron Approach. Pergamon Press,
New York; Inch TD (1984) Tetrahedron 40:3161;
Fraser-Reid B, Tsang R (1989) Strategies and
Tactics in Organic Synthesis. Academic Press,
New York
9. Mitsunobu O (1981) Synthesis 1
10. Castro BR (1983) Org React 29:1
11. Zottola MA, Alonso R, Vite GD, Fraser-Reid B
(1989) J Org Chem 54:6123
12. Bailliez V, de Figuiredo RM, Olesker A,
Cleophax J (2003) Synthesis 1015
13. Dromowicz M, Köll P (1998) Carbohydr Res
308:169
14. Wiggins LF (1963) Methods Carbohydr Chem
2:188; Whistler RL, Lake WC (1972) Methods
Carbohydr Chem 6:286
15. Lundt I, Skelbaek-Pedrsen B Acta Chim Scand
Ser B (1981) 35:637; Skelto B, Stick RV, Matthew
D (2000) Austr J Chem 53:389; Sridhar P, Saravanan V, Chandrasekarn S (2005) Pure Appl
Chem 77:145
16. Sivapriya K, Chandrasekaran S (2006) Carbohydr
Res 341:2204
17. Fuenets J, Olano D, Pradera MA Tetrahedron Lett
(1999) 40:4063
18. Krohn K, Gehle D, Flörke U (2005) Eur J Org
Chem 2841
19. Krohn K, Gehle D, Flörke U (2005) Eur J Org
Chem 4557
20. Witczak ZJ, Kaplon P, Kolodziej M (2002) J Carbohydr Chem 21:143
21. Kelly DR, Mahdi JG (2002) Tetrahedron Lett
43:511