By Peter G. M. Wuts, Theodora W. Greene(auth.)
The Fourth Edition of Greene's protecting teams in natural Synthesis is still an crucial reference for controlling the reactivity of the most typical sensible teams in the course of a man-made series. This new version comprises the numerous advancements within the box for the reason that e-book of the 3rd variation in 1998, including...
- New protecting teams equivalent to the fluorous family members and the uniquely detachable 2-methoxybenzenesulfonyl staff for the safety of amines
- New innovations for the formation and cleavage of latest protecting teams, with examples to demonstrate each one new strategy
- elevated assurance of the unforeseen facet reactions that happen with protecting teams
- New chart protecting the selective deprotection of silyl ethers
- 3,100 new references from the pro literature
The content material is geared up round the practical workforce to be safe, and levels from the easiest to the main advanced and hugely really good protecting groups.Content:
Chapter 1 The function of protecting teams in natural Synthesis (pages 1–15):
Chapter 2 safeguard for the Hydroxyl crew, together with 1,2? and 1,3?Diols (pages 16–366):
Chapter three security for Phenols and Catechols (pages 367–430):
Chapter four safety for the Carbonyl crew (pages 431–532):
Chapter five safeguard for the Carboxyl team (pages 533–646):
Chapter 6 safeguard for the Thiol staff (pages 647–695):
Chapter 7 safeguard for the Amino team (pages 696–926):
Chapter eight security for the Alkyne ?CH (pages 927–933):
Chapter nine safety for the Phosphate staff (pages 934–985):
Chapter 10 Reactivities, Reagents, and Reactivity Charts (pages 986–1051):
Read or Download Greene's Protective Groups in Organic Synthesis, Fourth Edition PDF
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Extra info for Greene's Protective Groups in Organic Synthesis, Fourth Edition
E. Greene, C. L. Drian, and P. Crabbe, J. Am. Chem. , 102, 7583 (1980). 25. D. B. Werz and P. H. Seeberger, Angew. Chem. Int. , 44, 6315 (2005). 26. R. M. Burk, T. S. Gac, and M. B. , 35, 8111 (1994). 27. V. Bethmont, F. Fache, and M. , 36, 4235 (1995). 28. H. Kotsuki, Y. Ushio, N. Yoshimura, and M. Ochi, J. Org. , 52, 2594 (1987). 29. H. Dvorakova, D. Dvorak, J. Srogl, and P. , 36, 6351 (1995). 30. For a review of alkyl ether cleavage, see B. C. Ranu and S. Bhar, Org. Prep. Proced. , 28, 371 (1996).
A requirement for the protective group on this hydroxyl was that it be removable (for the next condensation: 21 ϩ Troc-D-valine 22 → 23) under conditions that would leave unaltered the ϪCOOϪallyl, the N-Teoc, and the OTBS groups. The FMOC group (cleavage by piperidine) met this requirement. Choice of the Troc (2,2,2-trichloroethoxycarbonyl) group for N-protection of valine was based on the requirements of removability, without affecting OTBS and OTES groups, and stability to the conditions of removal of allyl from ϪCOOϪallyl [easily met by use of Pd(Ph3P) 4 for this deblocking].
Grealish, J. Org. , 66, 8640 (2001); P. L. DeRoy and A. B. Charette, Org. , 5, 4163 (2003). 19. J. Arnarp and J. Lönngren, Acta Chem. Scand. Ser. B, 32, 465 (1978). 20. R. E. Ireland, J. L. Gleason, L. D. Gegnas, and T. K. Highsmith, J. Org. , 61, 6856 (1996). 21. J. A. Marshall and S. Xie, J. Org. , 60, 7230 (1995). 22. K. Tomioka, M. Kanai, and K. , 32, 2395 (1991). 23. P. G. M. Wuts and S. R. Putt, unpublished results. 24. A. E. Greene, C. L. Drian, and P. Crabbe, J. Am. Chem. , 102, 7583 (1980).