(2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-tetrahydro-pyran | 934367-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-tetrahydro-pyran
• CAS: 934367-13-2
• 化学式: C₃₄H₃₃ClO₄
• 分子量: 541.087
• InChiKey: LGHBBQKMLXOPIL-CKOYEXALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.86
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-tetrahydro-pyran 在 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、253.33 kPa 条件下， 反应 3.0h， 以97%的产率得到(2R,3R,4R,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chlorobenzyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals

  摘要：

  Novel 2-deoxy-beta-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively beta anomers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.04.009
• 作为产物：
  描述：

  4-氯苯甲醛 、 (3,4,6-tri-O-benzyl-2-deoxy-α/β-D-galactopyranosyl)-triphenylphosphonium tetrafluoroborate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以70%的产率得到(2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-tetrahydro-pyran
  参考文献：
  名称：

  Stereoselective glycosidations of olefinated sugars

  摘要：

  The glycosidation of olefinated sugars using a catalytic amount of boron trichloride or triphenylphosphine hydrobromide proceeded in a highly stereoselective fashion to give the alpha anomers with good to high yields. The use of camphorsulphonic acid also afforded high stereoselectivity but lower yields were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02251-7