Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 20
37
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of 1,2-Epoxy-3-alkanols via Mitsunobu Reaction on Unprotected Enantiopure Acyclic 1,2,3-Triols

, &
Pages 2843-2850 | Received 29 Mar 1994, Published online: 23 Sep 2006

References

  • Gravier-Pelletier , C. , Sanière , M. , Charvet , I. , Le Merrer , Y. and Depezay , J. C. 1994 . Tetrahedron Lett. , 35 : 115 Preliminary communication
  • Bell , T. W. and Ciaccio , J. A. 1993 . J. Org. Chem. , 58 : 5153 For example, 38 to 53% yield was reported for selective tosylation of the primary hydroxyl group of RR-1, RS-1 respectively (R = C11H23) see
  • Attemps to selectively sulfonylate (ArSO2Cl, pyridine with Ar = 4-methoxyphenyl or 2,4,6-triisopropylphenyl) the primary hydroxyl group of SR-1 (R = (CH2)3CO2Et) in reasonable yield, failed
  • Mitsunobu , O. 1981 . Synthesis , : 1
  • Hughes , D. L. 1992 . Org. Reac. , 42 : 335 For a recent review see
  • McGowan , D. A. and Berchtold , G. A. 1981 . J. Org. Chem. , 46 : 2381
  • Abushanab , E. , Vemishetti , P. , Leiby , R. W. , Singh , H. K. , Mikkilineni , A. B. , Wu , D. C.J. , Saibaba , R. and Panzica , R. P. 1988 . J. Org. Chem. , 53 : 2598
  • Unambiguous proof of the structure of RR-2 and RS-2 (R = C10H21) was established both by comparison of their optical rotation with literature data (see experimental section), and by the synthesis of the corresponding 6-hydroxy-δ-valerolactones, to be published
  • Payne , G. B. 1962 . J. Org. Chem. , 27 : 3819
  • Gravier-Pelletier , C. , Dumas , J. , Le Merrer , Y. and Depezay , J. C. 1992 . J. Carbohydr. Chem. , 11 : 969 Enantiopure SS-3 ([α]D −34° (c1.02, CHCl3)) has already been prepared from ascorbic acid
  • Kang , S. K. , Kim , Y. S. , Lim , J. S. , Kim , K. S. and Kim , S. G. 1991 . Tetrahedron Lett. , 32 : 363
  • Mori , K. and Otsuka , T. 1983 . Tetrahedron , 39 : 3267
  • Barua , N. C. and Schmidt , R. R. 1986 . Tetrahedron , 42 : 4471
  • G C analysis was performed on a chiraldex column G-TA (30m × 0.25mm), temperature: 140°C, carrier gas: helium (800 Pa)

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.