(2R,3R,4R,5R,6R)-2-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol | 147624-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6R)-2-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol
• 英文别名: TBDMS(-3)[TBDMS(-4)][TBDMS(-6)]Glc(b)-O-Bn；(2R,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-phenylmethoxyoxan-3-ol
• CAS: 147624-51-9
• 化学式: C₃₁H₆₀O₆Si₃
• 分子量: 613.07
• InChiKey: SGCHXJYVYVLGKU-JQPIIJRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  (2R,3R,4R,5R,6R)-2-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol 在 钯 4-二甲氨基吡啶 、 Ph₃P-diethyl azodicarboxylate 、 氢气 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Total synthesis of (-)-ovatolide

  摘要：

  The total synthesis of (-)-ovatolide (1), a tetracyclic indole-containing beta-glucosyl derivative with an unusual pyrano[2,3-b][1,4]dioxocan-6-one system, is described. The beta-glucosidic linkage arose from regio- and stereocontrolled reaction of a protected 1,2-epoxyglucal derivative with 4-hydroxy-5-(benzyloxy)indole, and a lactonization reaction afforded the central dioxocanone system. An alternative strategy that afforded the tetracyclic framework as a mixture of epimers is also described.

  DOI：

  10.1021/jo00062a034
• 作为产物：
  描述：

  在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 、 (2R,3R,4R,5R,6R)-2-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  β-Glycosidation of Sterically Hindered Alcohols

  摘要：

  The 2-chloro-2-methylpropanoic ester serves as a steering group in the Schmidt glycosidation reaction. Rapid and efficient glycosidation of a range of sterically hindered alcohols takes place under mild, acidic conditions to afford the glycoside products in high yield and beta-selectivity and without formation of orthoester side products. The 2-chloro-2-methylpropanoic ester is readily cleaved under mild, basic conditions.

  DOI：

  10.1021/ol9000735