(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-but-3-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran | 485386-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-but-3-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran
• CAS: 485386-65-0
• 化学式: C₂₆H₃₂O₅
• 分子量: 424.537
• InChiKey: XACFRRZVDXOHRW-RTJMFUJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-but-3-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(2S,3R,4S,4aR,9aR)-3,4-Bis-benzyloxy-2-methoxy-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocycloheptene
  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 、 四丁基氟化铵 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-but-3-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran
  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