(7R,8S,9S)-9-tert-butyldimethylsilyloxy-2,6-dioxo-7,8-epoxy-1,3-dioxa-spiro[4.5]decane | 649572-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (7R,8S,9S)-9-tert-butyldimethylsilyloxy-2,6-dioxo-7,8-epoxy-1,3-dioxa-spiro[4.5]decane
• 英文别名: (1'R,5'S,6'S)-5'-[tert-butyl(dimethyl)silyl]oxyspiro[1,3-dioxolane-4,3'-7-oxabicyclo[4.1.0]heptane]-2,2'-dione
• CAS: 649572-55-4
• 化学式: C₁₄H₂₂O₆Si
• 分子量: 314.411
• InChiKey: RFEBTZJIEVRNOK-NOWMRDAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (7R,8S,9S)-9-tert-butyldimethylsilyloxy-2,6-dioxo-7,8-epoxy-1,3-dioxa-spiro[4.5]decane 在 chromium(VI) oxide 、 硫酸 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 17.5h， 生成 叶点霉素
  参考文献：
  名称：

  Total synthesis of (+)-epiepoformin and (−)-phyllostine

  摘要：

  An efficient asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine has been achieved using the chiral building block available from the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Since (-)-theobroxide was derived from the same precursor of (+)-epiepoformin, the formal total synthesis of (-)-theobroxide has also been achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.065
• 作为产物：
  描述：

  (-)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methylene-1-cyclohexanone 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (7R,8S,9S)-9-tert-butyldimethylsilyloxy-2,6-dioxo-7,8-epoxy-1,3-dioxa-spiro[4.5]decane
  参考文献：
  名称：

  Total synthesis of (+)-epiepoformin and (−)-phyllostine

  摘要：

  An efficient asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine has been achieved using the chiral building block available from the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Since (-)-theobroxide was derived from the same precursor of (+)-epiepoformin, the formal total synthesis of (-)-theobroxide has also been achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.065

文献信息

• Total synthesis of (+)-epiepoformin and (−)-phyllostine
  作者：Hiroaki Okamura、Hideki Shimizu、Naomi Yamashita、Tetsuo Iwagawa、Munehiro Nakatani

  DOI：10.1016/j.tet.2003.10.065

  日期：2003.12

  An efficient asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine has been achieved using the chiral building block available from the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Since (-)-theobroxide was derived from the same precursor of (+)-epiepoformin, the formal total synthesis of (-)-theobroxide has also been achieved. (C) 2003 Elsevier Ltd. All rights reserved.