By Peter G. M. Wuts, Theodora W. Greene
The Fourth Edition of Greene's protecting teams in natural Synthesis is still an critical reference for controlling the reactivity of the most typical useful teams in the course of an artificial series. This new version comprises the numerous advancements within the box on account that e-book of the 3rd variation in 1998, including...* New protecting teams resembling the fluorous kin and the uniquely detachable 2-methoxybenzenesulfonyl crew for the security of amines* New options for the formation and cleavage of present protecting teams, with examples to demonstrate every one new method* increased assurance of the unforeseen part reactions that happen with protecting teams* New chart overlaying the selective deprotection of silyl ethers* 3,100 new references from the pro literatureThe content material is geared up round the sensible staff to be secure, and levels from the best to the main advanced and hugely really good protecting groups.
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Additional info for Greene's Protective Groups in Organic Synthesis (4th Edition)
O CH2Cl2, H2O 88% OTBS OH 28 O O I2, sunlamp OTBDMS HO R=H CO2CH2CH2TMS MeO2C ninety two% R = SEM RO OMe thirteen. Pyridine·HF, THF, 2. five h, 0–25ЊC, seventy nine% yield. 29 14. CBr4, MeOH, reflux, 10–18 h, 88–98% yield. those stipulations produce HBr in situ. The TES, TBS, TBDPS, and suggestions ethers also are cleaved, but if IPA is used because the solvent suggestions and TBDPS ethers are strong. 30 15. A examine of the reductive cleavage of a sequence of alkoxymethyl ethers utilizing the glucose spine indicates that, reckoning on the reagent, first-class selectivity might be received for deprotection vs. methyl ether formation for many of the typical protecting teams. 31 OBn OBn BnO OBn MeO O hydride OR′ BnO MeO OBn O OR 1. R = H 2. R = Me Relative Cleavage charges for chosen Ethers of a major Alcohol AlH2Cl AlHCl2 BH3/THF BH3/Toluene Ether R' = percentage 1 percentage 2 percentage 1 percentage 2 percentage 1 percentage 2 percentage 1 percentage 2 MTM SEM BOM pAOM EOM a hundred zero zero forty five zero zero zero zero fifty five zero a hundred a hundred 89 32 a hundred zero zero eleven sixty eight zero eighty five a hundred ninety eight 12 zero 15 zero 2 86 zero a hundred a hundred a hundred zero a hundred zero zero zero a hundred zero 57 ETHERS For secondary derivatives, the selectivity and reactivity varies a little. To what quantity this can be a functionality of the hugely functionalized glucose spinoff has now not been decided. The desk lower than provides the cleavage selectivity for the next response. OBn OBn BnO OR′ MeO O hydride OBn BnO OR MeO OBn O 1. R = H 2. R = Me Relative Cleavage premiums of varied Ethers of a Secondary Alcohol AlH2Cl AlHCl2 BH3/THF BH3/Toluene Ether R' = percentage 1 percentage 2 percentage 1 percentage 2 percentage 1 percentage 2 percentage 1 percentage 2 SEM BOM pAOM EOM a hundred a hundred zero a hundred zero zero zero zero eighty two ninety zero a hundred 18 10 zero zero zero zero zero zero zero zero zero zero a hundred a hundred zero a hundred zero zero a hundred zero 1. See, for instance, Q. Zeng, S. Bailey, T. -Z Wang, and L. A. Paquette, J. Org. Chem. , sixty three, 137 (1998). 2. B. H. Lipshutz and J. J. Pegram, Tetrahedron Lett. , 21, 3343 (1980). three. okay. D. Freeman-Cook and R. L. Halcomb, J. Org. Chem. , sixty five, 6153 (2000). four. B. H. Lipshutz, R. Moretti, and R. Crow, Tetrahedron Lett. , 30, 15 (1989). five. D. R. Williams, P. A. Jass, H. -L. A. Tse, and R. D. Gaston, J. Am. Chem. Soc. , 112, 4552 (1990). 6. T. Wada, M. Tobe, T. Nagayama, ok. Furusawa, and M. Sekine, Tetrahedron Lett. , 36, 1683 (1995). 7. T. Kan, M. Hashimoto, M. Yanagiya, and H. Shirahama, Tetrahedron Lett. , 29, 5417 (1988). eight. B. H. Lipschutz and T. A. Miller, Tetrahedron Lett. , 30, 7149 (1989). nine. J. C. Craig and E. T. Everhart, Synth. Commun. , 20, 2147 (1990). 10. okay. Suzuki, T. Matsumoto, okay. Tomooka, ok. Matsumoto, and G. -I. Tsuchihashi, Chem. Lett. , sixteen, 113 (1987). eleven. R. E. eire, R. S. Meissner, and M. A. Rizzacasa, J. Am. Chem. Soc. , a hundred and fifteen, 7166 (1993). 12. ok. Jansson, T. Frejd, J. Kihlberg and G. Magnusson, Tetrahedron Lett. , 29, 361 (1988). For an different case, see R. H. Schlessinger, M. A. Poss, and S. Richardson, J. Am. Chem. Soc. , 108, 3112 (1986). thirteen. A. Hasegawa, Y. Ito, H. Ishida, and M. Kiso, J. Carbohydr. Chem. , eight, one hundred twenty five (1989); okay. Jansson, T. Frejd, J. Kihlberg, and G. Magnusson, Tetrahedron Lett. , 27, 753 (1986). 14. okay. P. R. Kartha, M. Kiso, and A. Hasegawa, J. Carbohydr. Chem. , eight, 675 (1989).