(2S,3R,6S,8S)-2-Methyl-3,6-epoxyundecane-1,8-diol | 128806-59-7

• 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: (2S,3R,6S,8S)-2-Methyl-3,6-epoxyundecane-1,8-diol
• 英文别名: (2R,3R,6S,8S)-3,6-epoxy-2-methylundecane-1,8-diol；(2S)-1-[(2S,5R)-5-[(2R)-1-hydroxypropan-2-yl]oxolan-2-yl]pentan-2-ol
• CAS: 128806-59-7
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: NTPHOIMOCITENQ-NOOOWODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (2S,3R,6S,8S)-2-Methyl-3,6-epoxyundecane-1,8-diol 在 吡啶 、 dipotassium hydrogenphosphate 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 三氟过氧乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ((2S)-cis-5-isopropyl-tetrahydro-furan-2-yl)-methanol
  参考文献：
  名称：

  pamamycin-607（绝对的立体化学），它是一种可引起阿尔博尼氏链霉菌的空中菌丝体诱导物质

  摘要：

  通过将其衍生为糠基化合物（14），已确定了帕马霉素-607的绝对立体化学（1），其旋光度与化学上衍生自非肌动蛋白抗生素的真实化合物的旋光度一致。

  DOI：

  10.1039/c39890001911
• 作为产物：
  描述：

  2-[(S)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-dihydro-furan-(2Z)-ylidene]-propionic acid tert-butyl ester 在 rhodium on alumina lithium aluminium tetrahydride 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 (2S,3R,6S,8S)-2-Methyl-3,6-epoxyundecane-1,8-diol
  参考文献：
  名称：

  Diastereodivergent synthesis of the C8–C18 precursor and C1′–C11′ subunit of pamamycin 607 induced by a chiral sulfoxide group

  摘要：

  A key step in obtaining the C8-C18 and C1'-C11' fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center alpha to the tetrahydrofuran ring, was the chelation controlled E-Z-isomerization of the substituted vinyl tetrahydrofuran intermediate 3a which has so far been obtained only in the more stable E-configuration. (C) 2000 Elsevier Science Ltd. Air rights reserved.

  DOI：

  10.1016/s0040-4039(00)00251-3

文献信息

• Stereoselective Synthesis of Pamamycin-607
  作者：Jeong、Eun Joo Kang、Lee Taek Sung、Sung Kil Hong、Eun Lee

  DOI：10.1021/ja0279646

  日期：2002.12.1

  A macrodiolide antibiotic pamamycin-607 was synthesized by joining two hydroxy acid components. Three cis-2, 5-disubstituted tetrahydrofuran rings in the molecule were stereoselectively prepared by radical cyclization reactions of beta-alkoxyvinyl ketone intermediates and a beta-alkoxymethacrylate substrate. The key step of the synthesis is characterized by the predominant threo product formation in

  通过连接两个羟基酸组分合成了大环内酯类抗生素 pamamycin-607。通过β-烷氧基乙烯基酮中间体和β-烷氧基甲基丙烯酸酯底物的自由基环化反应立体选择性地制备了分子中的三个顺式2、5-二取代四氢呋喃环。合成的关键步骤的特征是在 β-烷氧基甲基丙烯酸酯中间体的自由基环化反应中主要生成苏式产物。
• Total Synthesis of Pamamycin-607
  作者：Eun Lee、Jeong、Eun Joo Kang、Lee Taek Sung、Sung Kil Hong

  DOI：10.1021/ja016272z

  日期：2001.10.1

  Mycobacterium tuberculosis ) as well as against phytopathogenic fungi. Total synthesis of pamamycin-607 and other members of the family have not yet been communicated in the literature despite intense synthetic efforts, 3,4 and we wish to report here the results of our research which culminated in a total synthesis of pamamycin-607. In retrosynthetic analysis (Scheme 1), the ester bond formation between

  抗革兰氏阳性菌（包括结核分枝杆菌的多种抗生素耐药菌株）以及植物病原真菌。尽管进行了大量的合成努力，但 pamamycin-607 和其他家族成员的全合成尚未在文献中进行交流，3,4 我们希望在此报告我们的研究结果，该结果最终实现了 pamamycin-607 的全合成。在逆合成分析（方案 1）中，羧酸 A 和醇 E 之间的酯键形成将为制备 pamamycin-607 (1) 所需的最终大环二内酯环化奠定基础。酸A可以从酯D获得，采用关键的自由基环化反应5
• Total syntheses of pamamycin 607 and methyl nonactate: stereoselective cyclisation of homoallylic alcohols that had been prepared with remote stereocontrol using allylstannanes
  作者：Olivier Germay、Naresh Kumar、Christopher G. Moore、Eric J. Thomas

  DOI：10.1039/c2ob26801a

  日期：——

  then replaced by an N-(tert-butoxycarbonyl) group and O-debenzylation and oxidation gave the carboxylic acid 70 that corresponds to the C(1)–C(18) fragment of pamamycin 607 (1). Similar chemistry was used to prepare the C(1′)–C(11′) fragment 89 of the pamamycin, except that in this case the configuration of the secondary alcohol introduced by the allylstannane reaction had to be inverted using a Mitsunobu

  发现在路易斯酸存在下，使用苯基硒烯基氯或邻苯二甲酰亚胺，由氯化锡（IV）介导的（Z）-均烯丙基醇的环化反应，然后还原性去除苯基硒烯基，可得到具有优异立体控制的2,5-顺式-二取代四氢呋喃。 。使用该程序，通过锡（IV）立体选择性地制备了（2 S，4 S，8 R，6 Z）-9-苄氧基-2-叔丁基二苯基甲硅烷基氧基-8-甲基非-6-烯-4-醇（11））之间的氯化物促进反应（R）-5-苄氧基-4-甲基戊-2-烯基（三丁基）锡烷（3）和（S）-3-叔丁基二苯基甲硅烷基氧基丁醛（10），得到（2 S，3 R，6 S，8 S）-1脱硒后的-苄氧基-8-叔丁基二苯基甲硅烷氧基-3，6-环氧-2-甲基壬烷（13）。将该四氢呋喃选择性地脱保护，氧化和酯化，得到非乳酸甲酯（2）。已经建立了2，5-顺式-二取代的四氢呋喃的这种合成，将其用于完成帕马霉素607（1）的合成。（2 S，3 R从（R）立体选择性地制备，6S，8R）-1-苄氧基-8-
• Synthesis of the C1′–C11′ portion of pamamycin-607 via a stereoselective oxymercuration of a gamma—silyloxyallene and a stereospecific magnesium—methanol reduction
  作者：Robert D. Walkup、Gyoosoon Park

  DOI：10.1016/s0040-4039(00)80798-4

  日期：1988.1

  The C1′–C11′ portion of the antibiotic pamamycin-607, a novel homologue and C2-epimer of nonactic acid, was synthesized in six steps from 4,5-hexadien-1-ol via a novel -selective oxymercuration/transpalladation/methoxycarboxylation of a γ-silyloxyallene and a -selective reduction of a 2-(2-tetrahydrofuranyl)acrylate using magnesium in methanol. Spectroscopic properties of a derivative of the synthetic

  的C 1'〜C 11'的抗生素pamamycin-607，一种新颖的同系物和C的部分2 nonactic酸差向异构体，在六个步骤通过一种新颖的合成由4,5-己二烯-1-醇-选择性oxymercuration /使用甲醇中的镁，将γ-甲硅烷基氧丙烯烯进行palpalpalation /甲氧基羧化反应，并选择性地还原2-（2-四氢呋喃基）丙烯酸酯。合成℃的衍生物的光谱性质1' -C 11'部分匹配的材料从天然产物衍生的。
• Syntheses of the Lower Portions of the Pamamycins from .gamma.-(Silyloxy)allenes Using Stereoselective Cyclization, Reduction, and Aldehyde Addition Methodologies
  作者：Robert D. Walkup、Sang Woong Kim

  DOI：10.1021/jo00091a037

  日期：1994.6

  The pamamycins are a group of homologous macrodiolides produced by Streptomyces alboniger and Streptomyces aurantiacus JA 4570 which are remarkable for their autoregulatory, antifungal, antibacterial, and anion-transfering activities. The syntheses of the C-1'-C-11' (''lower'') portions of pamamycin-607, pamamycin-649A, pamamycin-635A, pamamycin-649B, and pamamycin-635B as the methyl esters 8 and 10-12 are reported. The C-9'-C-11', portions of these esters were introduced by chelation-controlled allylations of C-8' aldehyde intermediates derived from the C-8' alcohols 9 (whose synthesis has been previously reported) and 13-15 using allyltrimethylsilane in the presence of titanium(IV) chloride. The alcohols 13-15 were synthesized via cis selective cyclizations of the trimethylsilyl ether derivatives of the nonracemic gamma-hydroxy allenes 24, 30, and 31 using a one-pot oxymercuration/transpalladation/methoxycarbonylation reaction followed by a chelation-controlled conjugate reduction of the resulting acrylate intermediates. The gamma-hydroxy allene 24 was synthesized via an enzymatic resolution of the gamma-acetoxy allene 20, and the gamma-hydroxy allenes 30 and 31 were synthesized by asymmetric aldol reactions. During the syntheses of the products 14 and 15, chemoselective hydrolyses and reduction reactions were employed in order to differentiate a C-8' carboxyl group from the C-1' carboxyl group. Starting from simple allenyl alcohol starting materials, overall yields from 2% (in 14 steps, for 10) to 14% (in 9 steps, for 12) were observed for the production of the C-1'-C-11' portions of the pamamycins.