Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 7
1,160
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Rapid, Acid‐Mediated Deprotection of Silyl Ethers Using Microwave Heating

&
Pages 959-964 | Received 12 Oct 2005, Published online: 16 Aug 2006

References

  • Greene , T. W. and Wuts , P. G. M. 1999 . Protecting Groups in Organic Synthesis New York : Wiley‐Interscience .
  • Kocienski , P. J. 1994 . Protecting Groups Stuttgart : Thieme .
  • Nelson , T. D. and Crouch , R. D. 1996 . Selective deprotection of silyl ethers . Synthesis , : 1031 – 1069 .
  • Crouch , R. D. 2004 . Selective monodeprotection of bis‐silyl ethers . Tetrahedron , 60 : 5833 – 5871 .
  • Kappe , C. O. 2004 . Controlled microwave heating in modern organic synthesis . Angew. Chem., Intl. Ed. Eng. , 43 : 6250 – 6284 .
  • Blackwell , H. E. 2003 . Out of the oil bath and into the oven—microwave‐assisted combinatorial chemistry heats up . Org. Biomol. Chem. , 1 : 1251 – 1255 .
  • Lew , A. , Krutzik , P. O. , Hart , M. E. and Chamberlin , A. R. 2002 . Increasing rates of reaction: microwave‐assisted organic synthesis for combinatorial chemistry . J. Comb. Chem. , 4 : 95 – 105 .
  • Lidström , P. , Tierney , J. , Wathey , B. and Westman , J. 2001 . Microwave assisted organic synthesis—a review . Tetrahedron , 57 : 9225 – 9283 .
  • Heravi , M. M. , Hydarzadeh , F. , Farhangi , Y. and Ghassemzadeh , M. 2004 . Zeolite‐supported chromium(VI) oxide. A mild, efficient, and inexpensive reagent for oxidative deprotection of trimethylsilyl ethers under microwave irradiation . Phosphorus, Sulfur Relat. Elem. , 179 : 1473 – 1475 .
  • Heravi , M. M. , Oskooie , H. A. , Yazdanpanah , S. and Mojtahdei , M. 2004 . Oxidative deprotection of trimethylsilyl ethers using bismuth nitrate supported on montmorillonite K‐10 under microwave irradiation . J. Chem. Res. , : 129 – 130 .
  • Oskooie , S. , Hossein , A. , Heravi , M. M. , Sarmad , N. , Saednia , A. and Ghassemzadeh , M. 2003 . A rapid method for oxidative deprotection of trimethylsilyl ethers with wet alumina supported Dess‐Martin periodinane in solventless system under microwave irradiation . Indian J. Chem. Sec. B. , 42B : 2890 – 2891 .
  • Tajbakhsh , M. , Heravi , M. M. and Habibzadeh , S. 2003 . Efficient and selective oxidative deprotection of trimethylsilyl ethers using supported potassium ferrate under microwave irradiation . Phosphorus, Sulfur Relat. Elem. , 178 : 361 – 364 .
  • Heravi , M. M. , Ajami , D. , Ghassemzadeh , M. and Tabar‐Hydar , K. 2001 . Zeofen, an efficient reagent for oxidative deprotection of trimethylsilyl ethers under microwave irradiation in solventless system . Synth. Commun. , 31 : 2097 – 2100 .
  • Hajipour , A. R. , Mallakpour , S. E. , Baltork , I. M. and Adibi , H. 2001 . Oxidative deprotection of trimethylsilyl ethers, tetrahydropyranyl ethers and ethylene acetals with benzyltriphenylphosphonium peroxymonosulfate under microwave irradiation . Synth. Commun. , 31 : 1625 – 1631 .
  • Heravi , M. M. , Beheshtiha , Y. S. , Oskooi , S. H. A. , Shoar , R. H. and Khalilpoor , M. 2000 . Direct oxidative deprotection using montmorillonite‐supported ammonium chlorochromate under conventional heating and microwave irradiation in solventless system . Phosphorus, Sulfur Relat. Elem. , 161 : 251 – 255 .
  • Sharafi , T. and Heravi , M. M. 2004 . DABCO, a reagent for deprotection of benzylic trimethylsilyl ethers under microwave irradiation in a solventless system . Phosphorus, Sulfur Silicon Relat. Elem. , 179 : 2437 – 2440 .
  • Dehkordi , M. B. , Heravi , M. M. , Khosrofar , P. , Ziafat , A. and Ghassemzadeh , M. 2004 . Oxidative deprotection of trimethylsilyl ethers with hexamethylenetetramine‐bromine supported onto silica gel under microwave irradiation in solventless system . Phosphorus, Sulfur Silicon Relat. Elem. , 179 : 2595 – 2598 .
  • Mojtahedi , M. M. , Saidi , M. R. , Heravi , M. M. and Bolourtchian , M. 1999 . Microwave‐assisted deprotection of trimethylsilyl ethers under solvent‐free conditions catalyzed by clay or a palladium catalyst . Monash. Chem. , 130 : 1175 – 1178 .
  • Hajipour , A. R. , Mallakpour , S. E. , Mohammadpoor‐Baltork , I. and Khoee , S. 2002 . An efficient method for selective deprotection of trimethylsilyl ethers, tetrahydropyranyl ethers, ethylene acetals and ketals under microwave irradiation . Synth. Commun. , 32 : 611 – 622 .
  • Saxena , I. , Deka , N. , Sarma , J. C. and Tsuboi , S. 2003 . A convenient method for protection and deprotection of alcohols and phenols as alkylsilyl ethers catalyzed by iodine under microwave irradiation . Synth. Commun. , 33 : 4005 – 4011 .
  • Corey , E. J. and Venkateswarlu , A. 1972 . Protection of hydroxyl groups as tert‐butyldimethylsilyl derivatives . J. Am. Chem. Soc. , 94 : 6190 – 6191 .
  • Ogilvie , K. E. , Thompson , E. A. , Quilliam , M. A. and Westmore , J. B. 1974 . Selective protection of hydroxyl groups in deoxynucleosides using alkylsilyl reagents . Tetrahedron Lett. , : 2865 – 2868 .
  • Ramanjulu , J. M. , Ding , X. , Joullie , M. M. and Li , W.‐R. 1997 . Synthesis of a reduced ring analog of didemnin B . J. Org. Chem. , 62 : 4961 – 4969 .
  • Hart , B. P. , Verma , S. K. and Rapoport , H. A. 2003 . Asymmetric synthesis of the carbapenam core from serine . J. Org. Chem. , 68 : 187 – 190 .
  • Ali , S. M. and Georg , G. I. 1997 . Formal syntheses of cryptophycin A and arenastatin A . Tetrahedron Lett. , 38 : 1703 – 1706 .
  • Eggen , M. , Mossman , C. J. , Buck , S. B. , Nair , S. K. , Bhat , L. , Ali , S. M. , Reiff , E. A. , Boge , T. C. and Georg , G. I. 2000 . Total synthesis of cryptophycin‐24 (Arenastatin A) amenable to structural modifications in the C16 side chain . J. Org. Chem. , 65 : 7792 – 7799 .
  • Yokoshima , S. , Ueda , T. , Kobayashi , S. , Sato , A. , Kuboyama , T. , Tokuyama , H. and Fukuyama , T. 2002 . Stereocontrolled total synthesis of (+)‐vinblastine . J. Am. Chem. Soc. , 124 : 2137 – 2139 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.