(3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoic acid | 160239-73-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoic acid
• CAS: 160239-73-6
• 化学式: C₁₄H₂₂O₆Si
• 分子量: 314.411
• InChiKey: WDWNLQCVSPMBSP-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoic acid 在 mercury(II) perchlorate 、 2,4,6-三氯苯甲酰氯 、 氟化氢吡啶 、 三乙胺 、 calcium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 、 乙腈 为溶剂， 反应 17.55h， 生成 互变霉素
  参考文献：
  名称：

  A practical semi-synthesis of tautomycin using a hydrolysate of natural tautomycin

  摘要：

  A useful and brief semi-synthesis of tautomycin, which can be supplied a large quantity, has been achieved through the coupling reaction of the C21-C26 segment (an epoxide) with the C1-C20 segment (a dithiane), which was derived from the degradation of natural tautomycin, toward the conformational analysis of the C21-C26 moiety and the exploration of structure-activity relationships. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.097
• 作为产物：
  描述：

  3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-oxo-3-[(4R)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]propyl]-4-methylfuran-2,5-dione 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到(3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoic acid
  参考文献：
  名称：

  Synthetic studies on tautomycin

  摘要：

  The 2,3-disubstituted maleic anhydride segment of tautomycin has been synthesized in optically active form. Oxidation of 3,4-disubsrituted furan employing singlet oxygen completes the construction of the maleic anhydride moiety. Esterification of the maleic anhydride segment without protecting anhydride moiety resulted in the successful coupling reaction with fragment derived from tautomycin.

  DOI：

  10.1016/s0040-4020(01)85365-5

文献信息

• Synthesis of Okadaic Acid-Tautomycin Hybrid
  作者：Katsunori Tsuboi、Yoshiyasu Ichikawa、Minoru Isobe

  DOI：10.1055/s-1997-3257

  日期：1997.6

  One of the three spiro-segments in the synthesis of okadaic acid was synthesized under a new heteroconjugate addition strategy. Successive coupling of this spiro-segment with two tautomycin-synthetic segments afforded a hybrid molecule between okadaic acid and tautomycin.

  冈田酸合成中的三个螺环片段之一是通过新的杂化共轭加成策略合成的。该螺环片段与两个妥妥霉素合成片段连续偶联，形成冈田酸和妥妥霉素之间的混合分子。
• Total synthesis of (+)-tautomycin
  作者：Katsunori Tsuboi、Yoshiyasu Ichikawa、Yimin Jiang、Atsushi Naganawa、Minoru Isobe

  DOI：10.1016/s0040-4020(97)00230-5

  日期：1997.4

  The synthesis of Segment B/C corresponding to the C26 through to the C1 positions of tautomycin was achieved by coupling between Segment B (an epoxide) and Segment C (a sulfone carbanion) in the presence of boron trifluoride etherate (BF3·OEt2). Two routes have been developed in esterification of Segment A with Segment B/C. The first route employed Segment A with furan moiety as masked maleic anhydride

  在存在三氟化硼醚化物（BF 3 ·OEt 2）的情况下，通过段B（环氧化物）和段C（砜碳负离子）之间的偶合，可以合成对应于互变异构体C26至C1位置的B / C段）。在用链段B / C酯化链段A中已经开发出两种途径。第一种方法使用具有呋喃部分的A段作为掩蔽的马来酸酐。在第二种方法中，直接使用马来酸酐作为链段A来完成改进的合成。在最后一步用吡啶鎓聚（氟化氢）（HF-Py）去除甲硅烷基保护基团完成了互变霉素的全合成。
• Synthetic studies on tautomycin
  作者：Atsushi Naganawa、Yoshiyasu Ichikawa、Minoru Isobe

  DOI：10.1016/s0040-4020(01)85365-5

  日期：1994.1

  The 2,3-disubstituted maleic anhydride segment of tautomycin has been synthesized in optically active form. Oxidation of 3,4-disubsrituted furan employing singlet oxygen completes the construction of the maleic anhydride moiety. Esterification of the maleic anhydride segment without protecting anhydride moiety resulted in the successful coupling reaction with fragment derived from tautomycin.
• A practical semi-synthesis of tautomycin using a hydrolysate of natural tautomycin
  作者：Masakuni Kurono、Minoru Isobe

  DOI：10.1016/j.tet.2003.09.097

  日期：2003.11

  A useful and brief semi-synthesis of tautomycin, which can be supplied a large quantity, has been achieved through the coupling reaction of the C21-C26 segment (an epoxide) with the C1-C20 segment (a dithiane), which was derived from the degradation of natural tautomycin, toward the conformational analysis of the C21-C26 moiety and the exploration of structure-activity relationships. (C) 2003 Elsevier Ltd. All rights reserved.