2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose | 948036-11-1

• 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: 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose
• 英文别名: (2S,3S,4R,5R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
• CAS: 948036-11-1
• 化学式: C₃₅H₄₆O₆Si
• 分子量: 590.832
• InChiKey: PZIIGWDUFNWDPC-JJTSXQPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose 在 calcium sulfate 、 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以88%的产率得到(1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A

  摘要：

  A partially benzylated derivative of the anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving an intramolecular O-ketopyranosylation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.057
• 作为产物：
  描述：

  (2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol 在 palladium dichloride 吡啶 、 cerium(III) chloride 、 18-冠醚-6 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 acetate buffer 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 31.5h， 生成 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose
  参考文献：
  名称：

  Synthesis of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A

  摘要：

  A partially benzylated derivative of the anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving an intramolecular O-ketopyranosylation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.057

文献信息

• Synthesis of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A
  作者：Sho Matsuda、Kazuhide Matsumura、Mikio Watanabe、Takashi Yamanoi

  DOI：10.1016/j.tetlet.2007.06.057

  日期：2007.8

  A partially benzylated derivative of the anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving an intramolecular O-ketopyranosylation. (c) 2007 Elsevier Ltd. All rights reserved.