Iodine : A versatile reagent in carbohydrate chemistry IV. Per-O-Acetylation, regioselective acylation and acetolysis

Tetrahedron

Volumn 53, Issue 34, 1997, Pages 11753-11766

  Kartha, K P Ravindranathan ^a   Field, Robert A ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ACETYLATION; ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; DRUG PURIFICATION; IN VITRO STUDY; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 0000466390     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00742-4     Document Type: Article

References (39)

1. Presented in part at the XVIIIth International Carbohydrate Symposium, Milan, Italy, 1996. For part III see Kartha, K.P.R.; Aloui, M.; Field, R.A. Tetrahedron Lett., 1996, 37, 8807.
2. Presented in part at the XVIIIth International Carbohydrate Symposium, Milan, Italy, 1996. For part III see Kartha, K.P.R.; Aloui, M.; Field, R.A. Tetrahedron Lett., 1996, 37, 8807.
3. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
4. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
5. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
6. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
7. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
8. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
9. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
10. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
11. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
12. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
13. 2/Sm deacylation and dealkoxycarbonylation: Yanada, R.; Negoro, N.; Bessho, K.; Yanada K. Synlett., 1995, 1261; oxidation of sulfides to sulfoxides: Orito, K.; Hatekayama, T.; Takeo, M.; Suginome H. Synthesis, 1995, 1357; cleavage of pentenoyl amides: Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 7920; cleavage of TBDMS ethers: Vaino, A.R.; Szarek, W.A. J, Chem. Soc., Chem. Commun., 1996, 2351; cleavage of p-methoxybenzyl ethers: Vaino A.R.; Szarek, W.A. Synlett., 1995, 1157; formation of benzyl/allyl ethers: Lin, J.M.; Li, H.H.; Zhou, A.M. Tetrahedron Lett., 1996, 37, 5159; iodolactonisation: Kitagawa O., Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593; iodocyclisation: Jones, A.D.; Knight, D.W. J. Chem. Soc., Chem. Commun., 1996, 915; oxidative coupling of enolates: Langer, T.; Illich M.; Helmchen, G. Tetrahedron Lett., 1995, 36, 4409; and Kim, K.M.; Ryu E.K. Tetrahedron Lett., 1996, 37, 1441.
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32. This work will be presented in detail in due course.
33. It has been observed that steroidal alcohols such as cholesterol can also be acetylated with ease in virtually quantitative yields using iodine/acetic anhydride under mild conditions without affecting the unsaturation in their structure. This work, however, is not presented here.
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