(3aS,4R,8aS)-4-Benzyloxymethyl-2,2-dimethyl-3a,4,6,8a-tetrahydro-[1,3]dioxolo[4,5-c]oxepine | 257281-18-8

• 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: (3aS,4R,8aS)-4-Benzyloxymethyl-2,2-dimethyl-3a,4,6,8a-tetrahydro-[1,3]dioxolo[4,5-c]oxepine
• 英文别名: (3aS,4R,8aS)-2,2-dimethyl-4-(phenylmethoxymethyl)-3a,4,6,8a-tetrahydro-[1,3]dioxolo[4,5-c]oxepine
• CAS: 257281-18-8
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: WGJDOWMDXYPJCT-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,4R,8aS)-4-Benzyloxymethyl-2,2-dimethyl-3a,4,6,8a-tetrahydro-[1,3]dioxolo[4,5-c]oxepine 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 、 水 为溶剂， 以72%的产率得到(3aR,4R,7R,8R,8aS)-4-Benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]oxepine-7,8-diol
  参考文献：
  名称：

  A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates

  摘要：

  A ring closing metathesis (RCM)-osmylation sequence has been developed for the formation of highly oxygenated cyclic ethers from the corresponding acyclic dienes. A systematic examination of various substrates in this reaction revealed that the process is general in scope and is insensitive to the number of alkoxy substituents present. Subsequent osmylation of the metathesis product proceeds with excellent diastereoselectivity to furnish highly oxygenated oxepanes. These oxepanes represent one-carbon homologated carbohydrates. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01881-x
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 Grubbs catalyst first generation 、 三氟甲磺酸 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 生成 (3aS,4R,8aS)-4-Benzyloxymethyl-2,2-dimethyl-3a,4,6,8a-tetrahydro-[1,3]dioxolo[4,5-c]oxepine
  参考文献：
  名称：

  A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates

  摘要：

  A ring closing metathesis (RCM)-osmylation sequence has been developed for the formation of highly oxygenated cyclic ethers from the corresponding acyclic dienes. A systematic examination of various substrates in this reaction revealed that the process is general in scope and is insensitive to the number of alkoxy substituents present. Subsequent osmylation of the metathesis product proceeds with excellent diastereoselectivity to furnish highly oxygenated oxepanes. These oxepanes represent one-carbon homologated carbohydrates. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01881-x

文献信息

• A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates
  作者：Jerome C.Y. Wong、Patrick Lacombe、Claudio F. Sturino

  DOI：10.1016/s0040-4039(99)01881-x

  日期：1999.12

  A ring closing metathesis (RCM)-osmylation sequence has been developed for the formation of highly oxygenated cyclic ethers from the corresponding acyclic dienes. A systematic examination of various substrates in this reaction revealed that the process is general in scope and is insensitive to the number of alkoxy substituents present. Subsequent osmylation of the metathesis product proceeds with excellent diastereoselectivity to furnish highly oxygenated oxepanes. These oxepanes represent one-carbon homologated carbohydrates. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.