Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 3
119
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

A Facile Synthesis of (2R 3S)-1-Amino-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutane;A Useful Component Block of HIV Protease Inhibitor

, &
Pages 395-401 | Received 05 Jun 1997, Published online: 15 Aug 2006

References and Notes

  • Kick , E. K. and Ellman , J. A. 1995 . J. Med. Chem. , 38 : 1427 – 1430 .
  • Meady , N. and Castar , J. 1996 . Drug of Future , 21 : 600 – 609 . Several HIV protease inhibitor are undergoing clinical evaluation, as shown reference see
  • Kim , E. E. , Baker , C. , Dwyer , T. M. D. , Murcko , M. A. , Rao , B. G. , Tung , R. D. and Navia , M. A. 1995 . J. Am. Chem. Soc. , 117 : 1181 – 1182 .
  • Tung Murcko , R. D. and Bhisetti , M. A. G. R. 1994 . WO : Vertex Pharmaceuticaly Inc. . 9405639 [Chem. Abstr. 1995, 122, P81141j]
  • Evans , B. , Rittle , E. K. E. , Homnick , C. F. , Springer , J. P. , Hirshfield , J. and Veber , D. F. 1985 . J. Org. Chem. , 50 : 4615 – 4625 .
  • Takemoto , Y. , Matsumoto , T. , Ito , Y. and Terashima , S. 1991 . Chem. Pharm. Bull. , 39 : 2425 – 2428 .
  • Rich , D. H. , Sun , C Q. , Vara Prasd , J. V. N. , Pathiasseril , A. , To , M. V. , Marshall , G. R. , Clare , M. , Muller , R. A. and Houseman , K. 1991 . J. Med. Chem. , 34 : 1225 – 1228 .
  • Sasaki , H. , Kim , W-S. , Suzuki , T. , Shibasaki , M. , Mitsuda , M. , Hasegawa , J. and Ohashi , T. 1994 . Tetrahedron Letters , : 35 6123 – 6126 .
  • Barrish , J. C. , Gordon , E. , Alam , M. , Lin , P-F. , Bisacchi , G. S. , Chen , P. , Cheng , P. T. W. , Fritz , A. W. , Greytok , J. A. , Hermsmeier , M. A. , Humphreys , W. G. , Lis , K. A. , Marella , M. A. , Merchant , Z. , Mitt , T. , Morrison , R. A. , Obermeier , M. T. , Pluscec , J. , Skoog , M. , Slusarchyk , W. A. , Spergel , S. H. , Stevenson , J. M. , Sun , C-Q. , Sundeen , J. E. , Taunk , P. , Tino , J. A. , Warrack , B. M. , Colonno , R. J. and Zahler , R. 1994 . J. Med. Chem. , 37 : 1758 – 1768 .
  • Baker , D. C. and Putt , S. R. 1978 . Synthesis , : 478 – 479 .
  • Brillon , D. and Sauvé , G. 1992 . J. Org. Chem. , 57 : 1838 – 1842 .
  • The HPLC chromatogram showed two signals with tr = 9.9 and 10.6 min assignable to the (2R,3S) and (2S,3S)-diastereomer, respectively.
  • Kano , S. , Tanaka , Y. , Sugino , E. and Hibino , S. 1980 . Synthesis , : 695 – 697 . For an example for NaBH4-TiCl4 reduction of aromatic nitro compound
  • Reetz , M. T. , Drewes , M. W. , Matthews , B. R. and Lennick , K. 1989 . J. Chem. Soc., Chem. Commun. , : 1474 – 1475 .
  • The HPLC chromatogram showed two signals with tr = 13.9 and 15.1 min assignable to the (2S,3S)- and (2R,3S)-diastereomer, respectively.

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.