* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With triethylamine In tetrahydrofuran at 0 - 20℃; for 18 h;
Triethylamine was added to the solution of compound 2 (15 mmol, 3.98 g) and benzyl bromide (16.5 mmol, 2.82 g) in THF (25 mL) at 0 °C. After the mixture was stirred for 18 h at room temperature, the solvent was evaporated in vacuo. The residue was dissolved in 50 mL of CH2Cl2, washed with HCl (1 N), H2O, Na2CO3 (5percent), and H2O, and then dried over Na2SO4. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (hexane/AcOEt, 2:1) to afford (2S,4R)-1,2-dibenzyloxycarbonyl-4-hydroxypyrrolidine (compound 3) as pale yellow oil (2.66 g, yield 50percent).
250 g
With caesium carbonate In N,N-dimethyl-formamide at 22℃; for 5 h; Cooling with ice
To a 3 L round bottom flask were added (25,4R)-1-(benzyloxycarbonyl)-4- hydroxypyrrolidine-2-carboxylic acid (190.0 g, 716 mmol, 1.0 eq.), DMF (2.0 L) and C52CO3 (117 g, 358 mmol, 0.5 eq.). The resulting mixture was cooled in an ice-water bath and benzyl bromide (172 g, 1000 mmol, 1.4 eq.) was slowly added. After the addition, the resulting suspension was stirred at 22 °C for 5 h. The reaction mixture wasdiluted with water (5 L) and EtOAc (5 L). The aqueous layer was removed and the organic layer washed with brine (2 x 3L), dried over Mg504, filtered and concentrated under reduced pressure to provide 250 g of the title comround as an oil, which was used in the next step without purification. LCMS: MS = 377.9 (M+23).
Reference：
[1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 17, p. 2747 - 2760
[2] Journal of Organic Chemistry, 2001, vol. 66, # 3, p. 1038 - 1042
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 47, p. 9073 - 9077
[4] Synlett, 1999, # 9, p. 1465 - 1467
[5] Tetrahedron, 2008, vol. 64, # 10, p. 2480 - 2488
[6] Angewandte Chemie - International Edition, 2008, vol. 47, # 44, p. 8429 - 8432
[7] Advanced Synthesis and Catalysis, 2010, vol. 352, # 1, p. 108 - 112
[8] Tetrahedron Letters, 1994, vol. 35, # 3, p. 451 - 454
[9] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 5, p. 575 - 580
[10] Journal of Organic Chemistry, 2017, vol. 82, # 23, p. 12366 - 12376
[11] Tetrahedron, 1998, vol. 54, # 5-6, p. 981 - 996
[12] Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 5004 - 5007
[13] Synlett, 2010, # 13, p. 1943 - 1946
[14] Journal of Molecular Catalysis A: Chemical, 2012, vol. 363-364, p. 404 - 410,7
[15] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2787 - 2800
[16] Carbohydrate Research, 1996, vol. 286, p. 123 - 138
[17] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1096 - 1101
[18] Synlett, 2011, # 4, p. 503 - 507
[19] Macromolecules, 2010, vol. 43, # 15, p. 6374 - 6380
[20] Patent: US2013/65935, 2013, A1, . Location in patent: Paragraph 0097; 0098
[21] Patent: WO2018/20358, 2018, A1, . Location in patent: Page/Page column 85
2
[ 13139-17-8 ]
[ 88501-00-2 ]
[ 13500-53-3 ]
Reference：
[1] Journal of Organic Chemistry, 2004, vol. 69, # 23, p. 8077 - 8085
3
[ 541-41-3 ]
[ 100-51-6 ]
[ 13504-85-3 ]
[ 13500-53-3 ]
Reference：
[1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 10, p. 1395 - 1403
4
[ 100-51-6 ]
[ 13504-85-3 ]
[ 13500-53-3 ]
Reference：
[1] Journal of Organic Chemistry, 2007, vol. 72, # 24, p. 9353 - 9356
5
[ 501-53-1 ]
[ 13500-53-3 ]
Reference：
[1] Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 5004 - 5007
[2] Tetrahedron Letters, 1994, vol. 35, # 3, p. 451 - 454
[3] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2787 - 2800
[4] Canadian Journal of Biochemistry and Physiology, 1959, vol. 37, p. 583,584
[5] Synlett, 2011, # 4, p. 503 - 507
[6] Macromolecules, 2010, vol. 43, # 15, p. 6374 - 6380
[7] Journal of Molecular Catalysis A: Chemical, 2012, vol. 363-364, p. 404 - 410,7
[8] Journal of Organic Chemistry, 2017, vol. 82, # 23, p. 12366 - 12376
[9] Patent: WO2018/20358, 2018, A1,
[10] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 5, p. 575 - 580
[11] Patent: US2013/65935, 2013, A1,
6
[ 51-35-4 ]
[ 13500-53-3 ]
Reference：
[1] Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 5004 - 5007
[2] Tetrahedron Letters, 1994, vol. 35, # 3, p. 451 - 454
[3] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2787 - 2800
[4] Canadian Journal of Biochemistry and Physiology, 1959, vol. 37, p. 583,584
[5] Journal of Molecular Catalysis A: Chemical, 2012, vol. 363-364, p. 404 - 410,7
[6] Journal of Organic Chemistry, 2017, vol. 82, # 23, p. 12366 - 12376
[7] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 5, p. 575 - 580
[8] Patent: US2013/65935, 2013, A1,
7
[ 100-44-7 ]
[ 13504-85-3 ]
[ 13500-53-3 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 7, p. 1755 - 1760
[2] Canadian Journal of Biochemistry and Physiology, 1959, vol. 37, p. 583,584
(2S,4R)-1,2-dibenzyloxycarbonyl-4-(3-triethoxysilylpropylaminocarbonyloxy)pyrrolidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With triethylamine; In tetrahydrofuran; at 20℃; for 24h;Reflux;
The solution of compound 3 (10 mmol, 3.55 g), triethoxysilylpropyl isocyanate (15 mmol, 3.71 g), and triethylamine (20 mmol, 2.02 g) in THF (25 mL) was refluxed for 24 h and then cooled to room temperature. After removal of solvent under vaccum, the crude product was purified by column chromatography on silica gel (hexane/AcOEt, 3:1) to give 4.99 g of (2S,4R)-1,2-dibenzyloxycarbonyl-4-(3-triethoxysilylpropylaminocarboxy) pyrrolidine (compound 4) as a brown oil (yield 83%).
(R)-1-[(S)-2-({(2S,4S)-4-(5-Amino-pentanoyloxy)-1-[(S)-2-benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid[ No CAS ]
(R)-1-[(S)-2-({(2S,4S)-4-(5-Amino-pentanoylamino)-1-[(S)-2-benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid[ No CAS ]
(2S,4S)-4-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester[ No CAS ]
(2S,4S)-4-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester[ No CAS ]
(2S,4S)-4-[(2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester[ No CAS ]
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
