(2E,6R)-1-benzyloxy-3,7-dimethyl-2-octene-6,7-diol | 130790-60-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,6R)-1-benzyloxy-3,7-dimethyl-2-octene-6,7-diol
• 英文别名: (R,E)-8-benzyloxy-2,6-dimethyloct-6-ene-2,3-diol；(E,3R)-2,6-dimethyl-8-phenylmethoxyoct-6-ene-2,3-diol
• CAS: 130790-60-2
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: XJQJQVZHPATDQZ-WSYSLRRZSA-N

物化性质

• 沸点：
  419.5±45.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,6R)-1-benzyloxy-3,7-dimethyl-2-octene-6,7-diol 在 sodium periodate 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以84%的产率得到(E)-4-methyl-6-(phenylmethoxy)-4-hexenal
  参考文献：
  名称：

  海洋细胞毒剂（+）-curacin A的全合成

  摘要：

  描述了curacin A（一种与微管蛋白上的秋水仙碱结合位点相互作用的细胞毒性剂）的总合成。聚合合成利用天然产物和手性库起始原料（香叶醇，丝氨酸）和不对称合成（手性烯丙基硼烷加成，夏雷特环丙烷化）来获得对映体纯形式的各种手性片段。天然产物的组装涉及碳-碳键的形成（Julia偶联）和杂环的制备（Wipf噻唑啉合成）。

  DOI：

  10.1016/s0040-4020(97)00368-2
• 作为产物：
  描述：

  香叶醇 在 potassium osmate(VI) 、 甲基磺酰胺 sodium hydride 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 20.0h， 生成 (2E,6R)-1-benzyloxy-3,7-dimethyl-2-octene-6,7-diol
  参考文献：
  名称：

  衍生自1,5-二烯的二醇的氧化环化反应：使用四氧化oxide催化形成对映体纯的顺式四氢呋喃；（+）-顺式索拉明的形式合成。

  摘要：

  DOI：

  10.1002/anie.200500513

文献信息

• Convenient synthesis of chiral epoxyisoprenoids by yeast reduction
  作者：Kodama Mitsuaki、Minami Hiroyuki、Mima Yukiko、Fukuyama Yoshiyasu

  DOI：10.1016/s0040-4039(00)94489-7

  日期：1990.1

  The terminal double bond of acyclic isoprenoids was converted into chiral epoxide in high optical yield by using asymmetric reduction of α-ketol with baker's yeast.

  通过使用酵母将α-酮醇不对称还原，无环类异戊二烯的末端双键以高光学收率转化为手性环氧化物。
• Total Synthesis of Thyrsiferyl 23-Acetate, a Specific Inhibitor of Protein Phosphatase 2A and an Anti-Leukemic Inducer of Apoptosis
  作者：Isabel C. González、Craig J. Forsyth

  DOI：10.1021/ja000001r

  日期：2000.9.1

  A convergent synthetic entry to the squalenoid polyether system has been developed and applied to the biologically active marine natural products thyrsiferyl 23-acetate (la), thyrsiferol (Ib), thyrsiferyl 18-acetate (Ic), and thyrsiferyl 18,23-diacetate (Id). This involved the separate construction of two advanced intermediates representing the C1-C15 (4) and C16-C24 (5) domains, followed by their organochromium-mediated coupling, installation of the tertiary alcohol at C15, and manipulation of the C18 and C23 acetate moieties. The C1-C15 (4) intermediate containing the three tetrahydropyranyl rings (A-B-C) was derived from two preconstructed tetrahydropyran-containing units representing the functionalized A (C2-C6) and C (C10-C14) rings (6 and 7, respectively). The bromotetrahydropyranyl A ring was obtained via bromoetherification of the hydroxyalkene 16, which was synthesized from (2R,3R)-epoxy geraniol. The C ring was stereoselectively constructed by acid-catalyzed opening of the hydroxy epoxide 32, derived from D-glutamic acid. Intermediates 6 and 7 were-joined using organochromium conditions, and ketone and hydroxyl functionalities were installed at carbons:7 and 11, respectively. Closure of the B ring was accomplished stereoselectively by formation of species derived from a C7, C11 keto-alcohol and in situ reduction of a tetrahydropyranyl oxonium. The complementary tetrahydrofuran D (C19-C22) ring was obtained from a geraniol-derived tertiary hydroxy alkene (44) via a stereoselective Re(VII)-induced syn-oxidative cyclization. The side chain appended to the D ring was elaborated into trans-alkenyl iodide 5 under Takai reaction conditions. CrCl2-mediated coupling of aldehyde 4 containing the secondary bromide at C3 of the natural products, with iodide 5 bearing acetate moieties at C18 and C23, installed the C15-C16 carbon-carbon bond. The resultant C15 allylic carbinol was converted into an cr,P-saturated ketone, and the final methyl group was added stereoselectively using methylmagnesium bromide. Saponification of the C18 acetate yielded la, whereas cleavage of both C18 and C23 acetates gave the triol Ib. This modular entry into the squalenoid-polyether system may facilitate further evaluation of the antileukemic, apoptosis-inducing, protein serine/threonine phosphatase 2A inhibitory and anti-multidrug resistance activities of the thyrsiferol-derived natural products.
• KODAMA, MITSUAKI;MINAMI, HIROYUKI;MIMA, YUKIKO;FUKUYAMA, YOSHIYASU, TETRAHEDRON LETT., 31,(1990) N8, C. 4025-4026
  作者：KODAMA, MITSUAKI、MINAMI, HIROYUKI、MIMA, YUKIKO、FUKUYAMA, YOSHIYASU

  DOI：——

  日期：——
• Total synthesis of (+)-curacin A, a marine cytotoxic agent
  作者：Michael Z. Hoemann、Konstantinos A. Agrios、Jeffrey Aubé

  DOI：10.1016/s0040-4020(97)00368-2

  日期：1997.8

  The total synthesis of curacin A, a cytotoxic agent that interacts with the colchicine binding site on tubulin, is described. The convergent synthesis utilizes natural product and chiral pool starting materials (geraniol, serine) and asymmetric synthesis (chiral allylborane addition, Charette cyclopropanation) to procure the various chiral fragments in enantiomerically pure form. The assembly of the

  描述了curacin A（一种与微管蛋白上的秋水仙碱结合位点相互作用的细胞毒性剂）的总合成。聚合合成利用天然产物和手性库起始原料（香叶醇，丝氨酸）和不对称合成（手性烯丙基硼烷加成，夏雷特环丙烷化）来获得对映体纯形式的各种手性片段。天然产物的组装涉及碳-碳键的形成（Julia偶联）和杂环的制备（Wipf噻唑啉合成）。
• Oxidative Cyclization of Diols Derived from 1,5-Dienes: Formation of Enantiopurecis-Tetrahydrofurans by Using Catalytic Osmium Tetroxide; Formal Synthesis of (+)-cis-Solamin
  作者：Timothy J. Donohoe、Sam Butterworth

  DOI：10.1002/anie.200500513

  日期：2005.7.25