(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol | 615564-31-3

• 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)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol
• 英文别名: (2R,3R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-ol
• CAS: 615564-31-3
• 化学式: C₆₁H₆₄O₁₁
• 分子量: 973.173
• InChiKey: RHRMZAOXKLTKRF-HUKZKSJNSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  72
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以95%的产率得到海藻糖
  参考文献：
  名称：

  Formation of 1,1-α,α-Glycosidic Bonds By Intramolecular Aglycone Delivery. A Convergent Synthesis of Trehalose

  摘要：

  [GRAPHICS]We report a new synthesis of trehalose analogs that involves the use of intramolecular aglycone delivery for stereoselective formation of the 1,1-alpha,alpha-glycosidic bond. The glycosylation reaction afforded the desired isomer exclusively and in good yield.

  DOI：

  10.1021/ol034836t
• 作为产物：
  描述：

  1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 在 碘代三甲硅烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 37.0h， 生成 (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Formation of 1,1-α,α-Glycosidic Bonds By Intramolecular Aglycone Delivery. A Convergent Synthesis of Trehalose

  摘要：

  [GRAPHICS]We report a new synthesis of trehalose analogs that involves the use of intramolecular aglycone delivery for stereoselective formation of the 1,1-alpha,alpha-glycosidic bond. The glycosylation reaction afforded the desired isomer exclusively and in good yield.

  DOI：

  10.1021/ol034836t

文献信息

• Stereoselective Synthesis of 1,1′‐Disaccharides by Organoboron Catalysis
  作者：Sanae Izumi、Yusuke Kobayashi、Yoshiji Takemoto

  DOI：10.1002/anie.202004476

  日期：2020.8.10

  2‐dihydroxyglycosyl acceptors and glycosyl donors in the presence of a tricyclic borinic acid catalyst. In this reaction, the complexation of the diols and the catalyst is crucial for the activation of glycosyl donors, as well as for the 1,2‐cis‐configuration of the products. The anomeric stereochemistry of the glycosyl donor depends on the employed glycosyl donor. Applications of the produced 1,1′‐disaccharides are

  在三环硼酸催化剂存在下，通过使用1,2-二羟基糖基受体和糖基供体可以实现1,1'-二糖的高度立体选择性合成。在该反应中，二醇和催化剂的络合对于糖基供体的活化以及产物的1,2-顺式构型至关重要。糖基供体的异头立体化学取决于所用的糖基供体。还描述了产生的1,1'-二糖的应用。
• Formation of 1,1-α,α-Glycosidic Bonds By Intramolecular Aglycone Delivery. A Convergent Synthesis of Trehalose
  作者：Matthew R. Pratt、Clifton D. Leigh、Carolyn R. Bertozzi

  DOI：10.1021/ol034836t

  日期：2003.9.1

  [GRAPHICS]We report a new synthesis of trehalose analogs that involves the use of intramolecular aglycone delivery for stereoselective formation of the 1,1-alpha,alpha-glycosidic bond. The glycosylation reaction afforded the desired isomer exclusively and in good yield.