A stereodivergent synthesis of hydroxyethylene dipeptide isostere via highly diastereoselective epoxidation

Synlett

Volumn , Issue 20, 2005, Pages 3136-3138

  Lee, Kyu Woong ^a   Choi, Hyeong Wook ^a   Lee, Byung Han ^a   Choi, Bo Seung ^a   Chang, Jay Hyok ^a   Kim, Young Keun ^a   Lee, Jae Hoon ^a   Heo, Taeho ^a   Nam, Do Hyun ^a   Shin, Hyunik ^a  

^a LG Chemical Ltd   (South Korea)

Author keywords

Diastereoselective epoxidation; Epoxide ring opening; Hydroxyethylene isostere; Stereodivergent

Indexed keywords

DIPEPTIDE; EPOXIDE; ESTER; HYDROXYETHYLENE ISOSTERE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; EPOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 29744466334     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921907     Document Type: Article

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39. 3, 125 MHz): δ = 170.8, 155.8, 136.6, 136.5, 129.6, 128.7, 128.6, 128.2, 128.1, 127.0, 67.0, 57.6, 53.6, 52.0, 51.8, 39.5, 33.3.
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42. 3, 125 MHz): δ = 177.2, 156.7, 137.1, 136.4, 129.4, 128.8, 128.6, 128.2, 128.0, 126.9, 79.9, 54.9, 39.3, 28.7, 24.1; MS: m/z = 340 [M + H].
43. Casado-Bellver, F. J.; Gonzalez-Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650.
44. 3, 400 MHz): δ = 7.34-7.28 (5 H, m), 3.57 (3 H, s), 3.51 (1 H, m), 3.24 (1 H, dd, J = 13.6, 5.6 Hz), 2.95 (1 H, dd, J = 13.6, 8.8 Hz), 2.32 (2 H, m), 1.95-1.69 (4 H, m); MS: m/z = 222 [M + H]. (Chemical Equation Presented)
45. 3, 400 MHz): δ = 7.35-7.17 (5 H, m), 5.65 (1 H, br), 3.61 (1 H, m), 2.88 (1 H, dd, J = 13.6, 5.2 Hz), 2.62 (1 H, dd, J = 13.6, 9.2 Hz), 2.43-2.29 (2 H, m), 1.94 (2 H, m), 1.68 (1 H, m), 1.47 (1 H, m); MS: m/z = 190 [M + H]. (Chemical Equation Presented)
46. 3, 100 MHz): δ = 176.6, 165.9, 136.1, 132.7, 129.5, 128.8, 128.6, 128.3, 128.0, 127.0, 80.4, 60.4, 50.0, 30.9, 28.2, 24.7; MS: m/z = 340 [M + H].