(1R,3R,4R,6S)-4-phenylmethoxy-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptan-5-one | 1403608-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3R,4R,6S)-4-phenylmethoxy-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptan-5-one
• CAS: 1403608-92-3
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: GHTAWNLJCFTRLJ-QEUVDIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,6S)-4-phenylmethoxy-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptan-5-one 在 indium(III) bromide 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (S)-1,3-bis(benzyloxy)-1-(1-phenyl-1H-pyrrol-2-yl)Propan-2-one
  参考文献：
  名称：

  InBr₃-Mediated One-Pot Synthesis of 2-(Polyhydroxylatedalkyl)-N-aryl-/-alkylpyrroles from 1,2-Cyclopropa-3-pyranone and Amines

  摘要：

  An efficient one-pot synthesis of polyhydroxyalkyl-substituted pyrroles from 1,2-cyclopropa-3-pyranones with primary amines is reported. With 10% of InBr3 as the catalyst, both aryl- and alkylamines as well as various 1,2-cyclopropa-3-pyranones are well tolerated. This method is highly appealing because of its one-pot process, mild reaction conditions, substrate simplicity, and broad substrate scope.

  DOI：

  10.1021/ol401489x
• 作为产物：
  描述：

  4,6-di-O-benzyl-1,5-anhydro-2-deoxy-α-1,2-C-methylene-D-allopyranose 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到(1R,3R,4R,6S)-4-phenylmethoxy-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptan-5-one
  参考文献：
  名称：

  环戊糖基寡糖合成的扩环糖基化策略

  摘要：

  使用1，2-环丙烷化的糖作为糖基供体，并使用碳水化合物O-亲核试剂作为受体，进行一锅扩环糖基化反应，以提供吡喃糖和呋喃糖衍生物的庚烷己糖模拟物。通过采用分歧策略和迭代方案，该方法成功地扩展到了庚烷低聚糖的合成。

  DOI：

  10.1021/ol302677z

文献信息

• A one-pot septanoside formation and glycosylation of acyclic dithioacetals derived from 1,2-cyclopropanated sugars
  作者：Patteti Venukumar、Chalapala Sudharani、Perali Ramu Sridhar

  DOI：10.1039/c3cc49116a

  日期：——

  Ring opening of 3-oxo-1,2-cyclopropanated sugars with thiols leads to the serendipitous discovery of the synthesis of sugar based homologated acyclic dithioacetals. These acyclic dithioacetals were found to undergo one-pot septanoside formation followed by stereoselective glycosylation in the presence of glycosyl acceptors under glycosylation reaction conditions.

  3-氧代-1,2-环丙烷化的糖与硫醇的开环导致偶然发现了基于糖的同源无环二硫缩醛的合成。发现这些无环二硫缩醛在糖基化反应条件下，在存在糖基受体的情况下经历一锅的七糖苷的形成，然后进行立体选择性糖基化。
• InBr₃-Mediated One-Pot Synthesis of 2-(Polyhydroxylatedalkyl)-<i>N</i>-aryl-/-alkylpyrroles from 1,2-Cyclopropa-3-pyranone and Amines
  作者：Pingyuan Wang、Shanshan Song、Zehong Miao、Guangfu Yang、Ao Zhang

  DOI：10.1021/ol401489x

  日期：2013.8.2

  An efficient one-pot synthesis of polyhydroxyalkyl-substituted pyrroles from 1,2-cyclopropa-3-pyranones with primary amines is reported. With 10% of InBr3 as the catalyst, both aryl- and alkylamines as well as various 1,2-cyclopropa-3-pyranones are well tolerated. This method is highly appealing because of its one-pot process, mild reaction conditions, substrate simplicity, and broad substrate scope.
• A Ring Expansion–Glycosylation Strategy toward the Synthesis of Septano-oligosaccharides
  作者：Perali Ramu Sridhar、Patteti Venukumar

  DOI：10.1021/ol302677z

  日期：2012.11.2

  ring-expansion–glycosylation reaction was performed using 1,2-cyclopropanated sugars as glycosyl donors and carbohydrate O-nucleophiles as acceptors to provide septanohexose mimics of pyranose and furanose derivatives. The methodology was successfully extended to the synthesis of septano-oligosaccharides by adopting a divergent strategy as well as an iterative protocol.

  使用1，2-环丙烷化的糖作为糖基供体，并使用碳水化合物O-亲核试剂作为受体，进行一锅扩环糖基化反应，以提供吡喃糖和呋喃糖衍生物的庚烷己糖模拟物。通过采用分歧策略和迭代方案，该方法成功地扩展到了庚烷低聚糖的合成。