1,2,3,6-tetra-O-benzoyl-4-deoxy-α-L-threo-hex-4-enopyranose | 69534-71-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,6-tetra-O-benzoyl-4-deoxy-α-L-threo-hex-4-enopyranose
• 英文别名: [(2S,3R,4S)-2,3,4-tribenzoyloxy-3,4-dihydro-2H-pyran-6-yl]methyl benzoate
• CAS: 69534-71-0
• 化学式: C₃₄H₂₆O₉
• 分子量: 578.575
• InChiKey: PYGAZKOPSBNHEE-ZZMKVXQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,2,3,6-tetra-O-benzoyl-β-D-galactopyranose 在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 2-甲基四氢呋喃 为溶剂， 以78%的产率得到1,2,3,6-tetra-O-benzoyl-4-fluoro-β-glucopyranoside
  参考文献：
  名称：

  Syntheses and NMR characterizations of epimeric 4-deoxy-4-fluoro carbohydrates

  摘要：

  The synthesis and NMR characterizations of 1,2,3,6-tetra-O-benzoyl-4-deoxy-4-fluoro-beta-D-galactopyranoside, the 4-deoxy-4-fluoro epimer of an intermediate in the synthesis of a drug substance, needed for use as a potential impurity standard and to confirm the stereoselectivity of a key fluorination step, are described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.019

文献信息

• Process Development of Selectively Benzoylated and Fluorinated Glycosyl Donors
  作者：Franz J. Weiberth、Harpal S. Gill、Ying Jiang、George E. Lee、Philippe Lienard、Clive Pemberton、Matthew R. Powers、Witold Subotkowski、Witold Tomasik、Benoit J. Vanasse、Yong Yu

  DOI：10.1021/op100053k

  日期：2010.5.21

  Route selection, process development and large-scale preparation of selectively benzoylated and fluorinated D-glucopyranoses, required as glycosyl donors for the synthesis of the SGLT inhibitor SAR7226, are discussed.
• Blattner, Regine; Ferrier, Robert J.; Tyler, Peter C., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1535 - 1539
  作者：Blattner, Regine、Ferrier, Robert J.、Tyler, Peter C.

  DOI：——

  日期：——
• Syntheses and NMR characterizations of epimeric 4-deoxy-4-fluoro carbohydrates
  作者：Witold Subotkowski、Dirk Friedrich、Franz J. Weiberth

  DOI：10.1016/j.carres.2011.07.019

  日期：2011.11

  The synthesis and NMR characterizations of 1,2,3,6-tetra-O-benzoyl-4-deoxy-4-fluoro-beta-D-galactopyranoside, the 4-deoxy-4-fluoro epimer of an intermediate in the synthesis of a drug substance, needed for use as a potential impurity standard and to confirm the stereoselectivity of a key fluorination step, are described. (C) 2011 Elsevier Ltd. All rights reserved.