benzyl-4,6-O-benzylidene-2,3-diamino-2,3-dideoxy-α-D-glucopyranoside | 53910-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl-4,6-O-benzylidene-2,3-diamino-2,3-dideoxy-α-D-glucopyranoside
• 英文别名: Benzyl-2,3-diamino-4,6-O-benzyliden-2,3-didesoxy-α-D-glucopyranosid；benzyl 4,6-O-benzylidene-2,3-deoxy-2,3-diamino-α-D-glucoside；(4aR,6S,7R,8R,8aS)-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diamine
• CAS: 53910-44-4
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: OJLNDEYLFMDMER-NPKOBNKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl-4,6-O-benzylidene-2,3-diamino-2,3-dideoxy-α-D-glucopyranoside 在 三氟化硼乙醚 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 45.25h， 生成 Benzyl-4,6-di-O-acetyl-2-acetylamino-2,3-didesoxy-3-(ethoxalylamino)-α-D-glucopyranosid
  参考文献：
  名称：

  Reckendorf, Wolfgang Meyer zu; Weber, Rolf; Hehenberger, Helmut, Chemische Berichte, 1981, vol. 114, # 4, p. 1306 - 1317

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzyl-2-acetylamino-3-azido-4,6-O-benzyliden-2,3-didesoxy-α-D-glucopyranosid 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 benzyl-4,6-O-benzylidene-2,3-diamino-2,3-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Reckendorf, Wolfgang Meyer zu; Weber, Rolf; Hehenberger, Helmut, Chemische Berichte, 1981, vol. 114, # 4, p. 1306 - 1317

  摘要：

  DOI：

文献信息

• Novel chiral diimines and diamines derived from sugars in copper-catalysed asymmetric cyclopropanation
  作者：Carmela Borriello、Maria Elena Cucciolito、Achille Panunzi、Francesco Ruffo

  DOI：10.1016/s0957-4166(01)00438-4

  日期：2001.9

  New chiral diimino and diamino ligands derived from alpha -D-mannose and alpha -D-glucose are described. The ligands are obtained by introducing the appropriate nitrogen functions at C(2) and C(3) of the sugar rings. The ability of the new chelates to promote the asymmetric copper(I)-catalysed cyclopropanation of styrene has been investigated. The nature of both the sugars and the chelates is crucial in determining the enantioselectivity of the reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Bis(phosphinoamides) based on sugars for highly enantioselective allylic substitution: inversion of stereocontrol by switching from glucose to mannose
  作者：Francesco Ruffo、Raffaella Del Litto、Antonella De Roma、Alessandra D’Errico、Santo Magnolia

  DOI：10.1016/j.tetasy.2006.07.032

  日期：2006.9

  New chiral bis(phosphinoamides) based on glucose 1G and mannose 1M have been prepared. Their Pd complexes catalyze the asymmetric desymmetrization of meso-cyclopenten-2-ene-1,4-diol biscarbamate in high ee's (up to 97%). Glucose and mannose moieties selectively promote formation of the opposite enantiomers, as a consequence of inverted steric motifs around the metal center. (c) 2006 Elsevier Ltd. All rights reserved.
• Mn(III) complexes of chiral ‘salen’ type ligands derived from carbohydrates in the asymmetric epoxidation of styrenes
  作者：Carmela Borriello、Raffaella Del Litto、Achille Panunzi、Francesco Ruffo

  DOI：10.1016/j.tetasy.2003.12.018

  日期：2004.2

  A strategy for the synthesis of new chiral salen type ligands derived from alpha-D-glucose and alpha-D-mannose is described. The compounds were obtained by introducing appropriate functions at the C2 and C3 positions of the sugar ring. The efficiency of the complexes in the epoxidation of styrenes was also examined and shown to give good results, for example, cis-beta-methylstyrene was functionalised with ee's of up to 86%. (C) 2003 Elsevier Ltd. All rights reserved.
• Reckendorf, Wolfgang Meyer zu; Weber, Rolf; Hehenberger, Helmut, Chemische Berichte, 1981, vol. 114, # 4, p. 1306 - 1317
  作者：Reckendorf, Wolfgang Meyer zu、Weber, Rolf、Hehenberger, Helmut

  DOI：——

  日期：——