2(S)-2-O-(di-tert-butyl-O-triethylsilyl)silyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-4-ene | 644995-71-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2(S)-2-O-(di-tert-butyl-O-triethylsilyl)silyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-4-ene
• 英文别名: ditert-butyl-[[(2S)-2,3,6,7-tetrahydrooxepin-2-yl]methoxy]-triethylsilyloxysilane
• CAS: 644995-71-1
• 化学式: C₂₁H₄₄O₃Si₂
• 分子量: 400.75
• InChiKey: DTAVVQLLIKBUIM-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2(S)-2-O-(di-tert-butyl-O-triethylsilyl)silyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-4-ene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-1-(2,3,6,7-Tetrahydro-oxepin-2-yl)-methanol
  参考文献：
  名称：

  Diastereoselective formation of seven-membered oxacycles by ring-expansion of cyclopropanated galactal

  摘要：

  The cyclopropanation and ring-expansion of 4,6-O-di-(tert-butyl)silanediyl-D-galactal using catalytic amounts of TMSOTf and silated nucleophiles gave a range of substituted oxepanes. Good to excellent yields were obtained in addition to very high selectivities. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.222
• 作为产物：
  描述：

  1,5-anhydro-4,6-O-(di-tert-butyl)silanediyl-2-deoxy-D-lyxo-hex-1-enitol 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 diethylzinc 作用下， 生成 2(S)-2-O-(di-tert-butyl-O-triethylsilyl)silyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-4-ene
  参考文献：
  名称：

  Diastereoselective formation of seven-membered oxacycles by ring-expansion of cyclopropanated galactal

  摘要：

  The cyclopropanation and ring-expansion of 4,6-O-di-(tert-butyl)silanediyl-D-galactal using catalytic amounts of TMSOTf and silated nucleophiles gave a range of substituted oxepanes. Good to excellent yields were obtained in addition to very high selectivities. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.222

文献信息

• Mechanistic studies of rearrangements during the ring expansions of cyclopropanated carbohydrates
  作者：Rhys Batchelor、Joanne E. Harvey、Paul Teesdale-Spittle、John O. Hoberg

  DOI：10.1016/j.tetlet.2009.10.031

  日期：2009.12

  Deuterium-labeling studies have been performed on the ring expansion of cyclopropanated carbohydrates. From these studies, mechanisms have been proposed for two unusual rearrangements. In addition, a selective deprotection of the 1,3-di-tert-butylsilyl ether protecting group at the secondary position versus the primary position has been observed. This is a high yielding transformation with the potential

  已对环丙烷化碳水化合物的扩环进行了氘标记研究。从这些研究中，已经提出了两种异常重排的机制。另外，已经观察到在相对于主要位置的次要位置上的1，3-二叔丁基甲硅烷基醚保护基的选择性脱保护。这是一种高收率的转化方法，具有一般合成用途的潜力。
• Diastereoselective formation of seven-membered oxacycles by ring-expansion of cyclopropanated galactal
  作者：Rhys Batchelor、John O. Hoberg

  DOI：10.1016/j.tetlet.2003.09.222

  日期：2003.12

  The cyclopropanation and ring-expansion of 4,6-O-di-(tert-butyl)silanediyl-D-galactal using catalytic amounts of TMSOTf and silated nucleophiles gave a range of substituted oxepanes. Good to excellent yields were obtained in addition to very high selectivities. (C) 2003 Elsevier Ltd. All rights reserved.