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Commercial Fmoc-S-triphenylmethyl-cysteine was esterified with allyl alcohol, HOBt(N-hydroxybenzotriazole), HBTU [2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate]and DIEA, and N-deprotected to S-triphenylmethyl-cysteine allyl ester
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You S.-L., and Kelly J.W. J. Org. Chem. 68 (2003) 9506-9509 Commercial Fmoc-S-triphenylmethyl-cysteine was esterified with allyl alcohol, HOBt(N-hydroxybenzotriazole), HBTU [2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate]and DIEA, and N-deprotected to S-triphenylmethyl-cysteine allyl ester
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36
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71049174812
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note
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1/n. The 3D drawing is shown in the online Supplementary data.
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37
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71049132996
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note
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2 was ultimately produced in a substantial quantity (8%).
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38
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71049130170
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note
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D value was in fair agreement with that (+35.2) of the major dipeptide separately synthesized by high-pressure coupling of 4 and d-(Et)Cys(Trt)-OAll which was analogously prepared from Fmoc-d-Cys(Trt)-OH and allyl alcohol with HOBt, HBTU, and DIEA (see Ref. 6).
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39
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0017774822
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Wang S.-S., Gisin B.F., Winter D.P., Makofske R., Kulesha I.D., Tzougraki C., and Meienhofer J. J. Org. Chem. 42 (1977) 1286-1290
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