((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane | 485386-44-5

• 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,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
• CAS: 485386-44-5
• 化学式: C₂₈H₄₀O₅Si
• 分子量: 484.708
• InChiKey: IBRGAFNTCJTNJO-SEFGFODJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 在 Grubbs catalyst first generation 四丁基氟化铵 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,6R,8S,9R,10S)-9,10-bis(benzyloxy)-8-methoxy-2,7-dioxabicyclo[4.4.0]dec-4-ene
  参考文献：
  名称：

  Cross-metathesis and ring-closing metathesis of olefinic monosaccharides

  摘要：

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01617-9
• 作为产物：
  描述：

  2,3-二-o-苄基-alpha-d-吡喃葡萄糖苷甲酯 在 咪唑 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Cross-metathesis and ring-closing metathesis of olefinic monosaccharides

  摘要：

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01617-9