Synthesis
Fmoc(OTIPS) benzyl ester (0.87 g, 1.48 mmol) is dissolved in 7.4 mL dry CH2Cl2 under an argon atmosphere. The solution is cooled to 0°C and 7.4 mL of 40% (v/v) Piperidine solution in dry CH2Cl2 is added dropwise. After 15 min of stirring at 0°C, the mixture is concentrated in vacuo at 25°C to an oil and put immediately onto the silica column (cyclohexane/EtOAc 5: 1 + 0.5% NEt3, elution of product with 1: 1 + 0.5% NEt3). The yield of Fmoc-Thr-Obzl is 0.44 g (1.20 mmol, 81%) as a colorless oil.
References
[1] Tetrahedron, 2012, vol. 68, # 2, p. 697 - 704
[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 16, p. 2645 - 2657
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 145 - 156
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 7, p. 1978 - 1987
[5] ChemBioChem, 2017, vol. 18, # 6, p. 527 - 538
