By Peter G. M. Wuts, Theodora W. Greene
The Fourth Edition of Greene's protecting teams in natural Synthesis remains to be an critical reference for controlling the reactivity of the most typical useful teams in the course of an artificial series. This re-creation comprises the numerous advancements within the box for the reason that ebook of the 3rd variation in 1998, including...* New protecting teams resembling the fluorous relatives and the uniquely detachable 2-methoxybenzenesulfonyl team for the safety of amines* New strategies for the formation and cleavage of present protecting teams, with examples to demonstrate every one new process* improved assurance of the unforeseen facet reactions that happen with protecting teams* New chart masking the selective deprotection of silyl ethers* 3,100 new references from the pro literatureThe content material is prepared round the sensible team to be safe, and levels from the easiest to the main advanced and hugely really good protecting groups.
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Extra info for Greene's Protective Groups in Organic Synthesis (4th Edition)
Tao, S. Daigneault, and Y. J. Meignam, J. Am. Chem. Soc. , a hundred and twenty, 10332 (1998). three. D. L. J. Clive and S. solar, Tetrahedron Lett. , forty two, 6267 (2001). four. I. Bajza, Z. Varga, and A. Liptak, Tetrahedron Lett. , 34, 1991 (1993). Guaiacolmethyl Ether (GUMϪOR): 2-MeOC6H4OCH2OR Formation/Cleavage OMe OCH2Cl 50% NaOH, PhH OMe ROH OCH2OR Bu4NHSO4, >80% ZnBr2, CH2Cl2, >80% it's attainable to introduce this crew selectively onto a prime alcohol within the presence of a secondary alcohol. The spinoff is strong to KMnO4, m-chloroperoxybenzoic acid, LiAlH4, and CrO3·Pyr. for the reason that this by-product is identical to the p-methoxyphenyl ether it's going to even be attainable to take away it oxidatively. The GUM ethers are much less sturdy than the MEM ethers in acid yet have related balance to the SEM ethers. it truly is attainable to take away the GUM ether within the presence of a MEM ether. 1 1. B. Loubinouz, G. Coudert, and G. Guillaumet, Tetrahedron Lett. , 22, 1973 (1981). ETHERS forty seven [(p-Phenylphenyl)oxy]methyl Ether (POMϪOR): 4-C6H5C6H4OCH2OR This team was once built to impart crystallinity to an intermediate in a synthesis of PNU-140690. The by-product is shaped from POMCl (from a threeњ alcohol: toluene, DIPEA, reflux, five h, seventy six% yield) and will be cleaved with H2SO4 (THF, MeOH, rt, eighty four% yield). 1 1. ok. S. Fors, J. R. Gage, R. F. Heier, R. C. Kelly, W. R. Perrault, and N. Wicienski, J. Org. Chem. , sixty three, 7348 (1998). t-Butoxymethyl Ether: t-BuOCH2OR the good thing about this ether is that it may be brought below quite impartial stipulations while the t-Bu team is brought less than acidic stipulations, yet will be cleaved through normal stipulations used to cleave the t-Bu ether. Formation 1. t-BuOCH2Cl,1 Et3N, Ϫ20ЊC → 20ЊC, three h, 54–80% yield. 2 2. t-BuOCH2SO2Ph, LiBr, TEA, toluene, 2–4 days, 70–92% yield. three three. t-BuOCH2SCH2CH3, CuBr2, TBAB, MS4, CH2Cl2, rt, four h, 69–91% yield. four Cleavage CF3COOH, H2O, 20ЊC, forty eight h, 85–90% yield. 2 The t-butoxymethyl ether is solid to scorching glacial acetic acid; aqueous acetic acid, 20ЊC; and anhydrous trifluoroacetic acid. 1. For a higher training of this reagent, see J. H. Jones, D. W. Thomas, R. M. Thomas, and M. E. wooden, Synth. Commun. , sixteen, 1607 (1986). 2. H. W. Pinnick and N. H. Lajis, J. Org. Chem. , forty three, 3964 (1978). three. M. Julia, D. Uguen, and D. Zhang, Synlett, 503 (1991). four. D. Sawada and Y. Ito, Tetrahedron Lett. , forty two, 2501 (2001). 4-Pentenyloxymethyl Ether (POMϪOR)1: CH2ϭCHCH2CH2CH2OCH2OR Formation POMCl, (i-Pr)2NEt, CH2Cl2. 2 The similar pentenyl glycosides, ready by means of the standard tools, have been used to guard the anomeric heart. 2 Cleavage NBS, CH3CN, H2O, 62–90% yield. 2–4 The POM crew has been selectively got rid of within the presence of an ethoxyethyl ether, TBDMS ether, benzyl ether, p-methoxybenzyl ether, an acetate, and an allyl staff. as the hydrolysis of a 48 safety FOR THE HYDROXYL workforce, together with 1,2- AND 1,3-DIOLS pentenyl 2-acetoxyglycoside was once rather a lot slower than a pentenyl 2-benzyloxyglycoside, the 2-benzyl spinoff may be cleaved selectively within the presence of the 2-acetoxy by-product. five The POM workforce is good to seventy five% AcOH yet is cleaved by way of five% HCl.
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