(4S)-4,6-bis((tert-butyldimethylsilyl)oxy)hexane-1,2-diol | 1361130-10-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4S)-4,6-bis((tert-butyldimethylsilyl)oxy)hexane-1,2-diol
• CAS: 1361130-10-0
• 化学式: C₁₈H₄₂O₄Si₂
• 分子量: 378.7
• InChiKey: GTZNARMGHMQDRT-LYKKTTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S)-4,6-bis((tert-butyldimethylsilyl)oxy)hexane-1,2-diol 在 sodium periodate 、 锂硼氢 、 2,6-二叔丁基吡啶 、 四氯化钛 、 戴斯-马丁氧化剂 、 (+)-鹰爪豆碱 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 23.5h， 生成 (2R,3S,5S)-5,7-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-2-methylheptanal
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluations of Aplyronine A–Mycalolide B Hybrid Compound

  摘要：

  A hybrid compound consisting of aplyronine A and mycalolide B was synthesized, and its biological activities were evaluated. The hybrid compound was found to have somewhat more potent actin-depolymerizing activity than aplyronine A. In contrast, the hybrid compound possessed about 1000-fold less cytotoxicity than aplyronine A. These results indicated that there is no direct correlation between actin-depolymerizing activity and cytotoxicity.

  DOI：

  10.1021/ol300182r
• 作为产物：
  描述：

  (5R)-2,2,3,3,9,9,10,10-octamethyl-5-(prop-2-en-1-yl)-4,8-dioxa-3,9-disilaundecane 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (4S)-4,6-bis((tert-butyldimethylsilyl)oxy)hexane-1,2-diol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluations of Aplyronine A–Mycalolide B Hybrid Compound

  摘要：

  A hybrid compound consisting of aplyronine A and mycalolide B was synthesized, and its biological activities were evaluated. The hybrid compound was found to have somewhat more potent actin-depolymerizing activity than aplyronine A. In contrast, the hybrid compound possessed about 1000-fold less cytotoxicity than aplyronine A. These results indicated that there is no direct correlation between actin-depolymerizing activity and cytotoxicity.

  DOI：

  10.1021/ol300182r

文献信息

• Total Synthesis and Tentative Structural Elucidation of Cryptomoscatone E3: Interplay of Experimental and Computational Studies
  作者：Luiz F. T. Novaes、Ariel M. Sarotti、Ronaldo A. Pilli

  DOI：10.1021/acs.joc.5b01956

  日期：2015.12.18

  A successful combination of computational chemistry and total synthesis was explored to tentatively elucidate the absolute configuration of cryptomoscatone E3, a polyketide isolated from the Brazilian tree Cryptocarya mandiocanna. Two independent synthetic approaches are discussed based on asymmetric allylation, ring closing metathesis, and aldol reactions.