2-((1R,2R)-2-Hydroxy-1-methyl-propyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester | 880766-70-1

• 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: 2-((1R,2R)-2-Hydroxy-1-methyl-propyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 2-[(2R,3R)-3-hydroxybutan-2-yl]cyclopropane-1,1-dicarboxylate
• CAS: 880766-70-1
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: RSDYQGKXXXZSLQ-KJFJCRTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((1R,2R)-2-Hydroxy-1-methyl-propyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 33.0h， 生成 Trifluoro-methanesulfonic acid (5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl ester
  参考文献：
  名称：

  Total Synthesis of (+)-Mycalamide A

  摘要：

  A convergent total synthesis of (+)-mycalamide A is described. A Yb(OTf)(3)-TMSCI catalytic system is used to synthesize a trioxadecalin ring system, which contains the right segment of mycalamide A. In addition, a tetrallydropyran ring, which is the left segment, is constructed with use of a novel one-pot delta-lactonization protocol. Both segments are prepared from a common starting material, D-mannitol. These segments are then coupled and the functional groups are transformed to synthesize (+)-mycalamide A.

  DOI：

  10.1021/ol052943c
• 作为产物：
  描述：

  (-)-(2R,3R,4R)-4-(4-methoxybenzyl)oxy-3-methylpentane-1,2-diol 在 palladium(II) acetate 、 正丁基锂 、 硝酸铵 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 17.83h， 生成 2-((1R,2R)-2-Hydroxy-1-methyl-propyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Total Synthesis of (+)-Mycalamide A

  摘要：

  A convergent total synthesis of (+)-mycalamide A is described. A Yb(OTf)(3)-TMSCI catalytic system is used to synthesize a trioxadecalin ring system, which contains the right segment of mycalamide A. In addition, a tetrallydropyran ring, which is the left segment, is constructed with use of a novel one-pot delta-lactonization protocol. Both segments are prepared from a common starting material, D-mannitol. These segments are then coupled and the functional groups are transformed to synthesize (+)-mycalamide A.

  DOI：

  10.1021/ol052943c

文献信息

• Convergent Total Synthesis of (+)-Mycalamide A
  作者：Natsuko Kagawa、Masataka Ihara、Masahiro Toyota

  DOI：10.1021/jo060803q

  日期：2006.9.1

  The details of a convergent total synthesis of (+)-mycalamide A are described. Yb(OTf)3−TMSCl-catalyzed cross-aldol reaction conditions are used to synthesize the right segment of mycalamide A. In this reaction, an acid-sensitive aldehyde reacts with methyl trimethylsilyl dimethylketene acetal without epimerization to provide the desired aldol adduct. Additionally, a tetrahydropyran ring, which is

  描述了（+）-mycalamide A的收敛全合成的细节。使用Yb（OTf）3 -TMSCl催化的交叉醇醛缩合反应条件来合成正确的mycalamide A链段。在该反应中，酸敏感性醛与甲基三甲基甲硅烷基二甲基乙烯酮缩醛反应而没有差向异构化，从而提供所需的醛醇加合物。另外，使用新颖的一锅δ-内酯形成方法制备了四氢吡喃环，其是mycalamide A的左段。两个片段均由常见的起始原料d-甘露糖醇构成。然后在BuLi的存在下将这些片段偶联，然后将官能团转化以完成（+）-mycalamide A的合成。
• Total Synthesis of (+)-Mycalamide A
  作者：Natsuko Kagawa、Masataka Ihara、Masahiro Toyota

  DOI：10.1021/ol052943c

  日期：2006.3.2

  A convergent total synthesis of (+)-mycalamide A is described. A Yb(OTf)(3)-TMSCI catalytic system is used to synthesize a trioxadecalin ring system, which contains the right segment of mycalamide A. In addition, a tetrallydropyran ring, which is the left segment, is constructed with use of a novel one-pot delta-lactonization protocol. Both segments are prepared from a common starting material, D-mannitol. These segments are then coupled and the functional groups are transformed to synthesize (+)-mycalamide A.