Stereo-conserved synthesis of syn-diarylheptanoids, active principles of Zingiber, starting from d-glucose

Tetrahedron Letters

Volumn 52, Issue 26, 2011, Pages 3397-3400

  Bhosale, Sandeep ^a   Vyavahare, Vinod P ^a   Prasad, Uppuleti Viplava ^b   Palle, Venkata P ^a   Bhuniya, Debnath ^a  

^a Advinus Therapeutics Private Limited Bangalore   (India)

^b ANDHRA UNIVERSITY   (India)

Author keywords

d Glucose; Syn diarylheptanoid; Wilkinson's catalyst; Wittig reaction

Indexed keywords

ALDEHYDE DERIVATIVE; GINGER EXTRACT; GLUCOSE; HEPTANE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHIRALITY; DRUG SYNTHESIS; DRUG TRANSFORMATION; GINGER; OLEFINATION; STEREOCHEMISTRY; WITTIG REACTION;

ZINGIBER;

EID: 79957602919     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.097     Document Type: Article

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26. 3): δ 26.36, 26.89, 40.41, 56.16, 71.13, 73.96, 80.97, 105.55, 111.03, 112.53, 113.70, 121.84, 127.47(2C), 127.63, 128.07, 128.79 (2C), 129.89, 134.74, 137.25, 147.87, 149.51. HPLC-MS (m/z): 400.3 [M+18] base peak, HPLC purity: 99.0%, rt: 15.6 min.
27. 3): δ 26.18, 26.76, 39.87, 55.98, 70.99, 78.70, 80.67, 105.43, 109.37, 111.09, 113.76, 119.90, 125.54, 127.29 (2C), 127.93, 128.63(2C), 129.96, 132.54, 137.06, 148.22, 149.68. HPLC-MS (m/z): 383.2 [M+1], 400.2 [M+18] base peak, purity: 99.44%, rt: 17 min.
28. A. Jourdant, E. González-Zamora, and J. Zhu J. Org. Chem. 67 2002 3163 3164
29. 3): δ 26.44, 26.92, 32.30, 36.43, 39.26, 56.24, 71.57, 77.36, 80.86, 105.55, 111.06, 112.76, 114.74, 120.50, 127.55(2C), 127.99, 128.74 (2C), 135.39, 137.74, 146.71, 149.93. HPLC-MS (m/z): 402.3 [M+18] base peak, HPLC purity: 97%, rt: 15.66 min.
30. 3): δ [31.92, 32.21, 37.71, 38.06, 38.53, 39.52 account for 3C)], 56.21, 71.40, 71.82 (0.7C), 76.48 (0.7C), 76.80 (0.3C), 79.42 (0.3C), 96.97 (0.7C), 102.81 (0.3C), 112.60, 114.46, 120.45, 127.55 (2C), 128.00, 128.71 (2C), 135.18, 137.50, 146.55, 149.71. HPLC-MS (m/z): 362.2 [M+18] base peak, HPLC purity: 94.0%, rt: 11.68 min.
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32. -1.
33. 3): δ 31.38, 39.83, 43.17, 56.03, 69.03, 71.24, 71.71, 112.32, 114.27, 120.26, 127.35 (2C), 127.47, 127.84, 128.48 (2C), 128.60 (2C), 128.83 (2C), 130.84, 133.88, 135.22, 136.49, 137.45, 146.40, 149.63. HPLC-MS (m/z): 436.2 [M+18] base peak, HPLC purity: 98.52%, rt: 16.27 min.