(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-hex-5-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran | 485386-67-2

• 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-hex-5-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran
• CAS: 485386-67-2
• 化学式: C₂₈H₃₆O₅
• 分子量: 452.591
• InChiKey: OTAKESRXZQLSBP-DFLSAPQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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-hex-5-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到(Z)-(2S,3R,4S,4aR,11aR)-3,4-Bis-benzyloxy-2-methoxy-3,4,4a,6,7,8,9,11a-octahydro-2H-1,5-dioxa-benzocyclononene
  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：

  (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran 在 camphor-10-sulfonic acid 、 四丁基氟化铵 、 sodium hydride 作用下， 以 甲醇 为溶剂， 生成 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-hex-5-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