Methanesulfonic acid (S)-1-methyl-pent-2-ynyl ester | 259175-58-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (S)-1-methyl-pent-2-ynyl ester
• 英文别名: [(2S)-hex-3-yn-2-yl] methanesulfonate
• CAS: 259175-58-1
• 化学式: C₇H₁₂O₃S
• 分子量: 176.236
• InChiKey: ZCDABFPZTUXTTL-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (S)-1-methyl-pent-2-ynyl ester 在 Lindlar's catalyst sodium hypochlorite 、 正丁基锂 、 Jacobsen's catalyst 、 copper(I) bromide dimethylsulfide complex 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 氢气 、 三正丁基氢锡 、 二异丙胺 作用下， 反应 0.17h， 生成 (2R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((2S,3R)-3-ethyl-oxiranyl)-2-methyl-pentan-3-ol
  参考文献：
  名称：

  Synthesis of a syn,syn,syn,syn-Stereopentad Precursor of the Marine Sponge Polyketide Callystatin A

  摘要：

  A C13-22 syn,syn,syn,syn-stereopentad precursor of the cytotoxic polyketide callystatin A has been prepared. The synthesis involved BF3-promoted addition of the (M)-allenylstannane 28 to the alpha-methyl-beta-OTBS aldehyde 8 to afford the syn,syn adduct homopropargylic alcohol 29. Protection as the cyclic anisylidene acetal 31 and reduction of the acetylenic triple bond with Red-Al gave the (E)-allylic alcohol 32. This was subjected to Sharpless asymmetric epoxidation and subsequent treatment with an ethylcopper reagent to yield diol 34; hydrogenolysis of the derived tosylate 37 with LiBEt3H afforded 38. Acetal hydrogenolysis with DIBAl-H and oxidation yielded aldehyde 40 which was subjected to Horner-Emmons homologation to afford ester 41. This ester was converted to ester 44, an intermediate in the Kobayashi synthesis, with which it was found to be identical.

  DOI：

  10.1021/jo9902143
• 作为产物：
  描述：

  tert-butyl-[(2S)-hex-3-yn-2-yl]oxy-dimethylsilane 在 四丁基氟化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Methanesulfonic acid (S)-1-methyl-pent-2-ynyl ester
  参考文献：
  名称：

  Synthesis of a syn,syn,syn,syn-Stereopentad Precursor of the Marine Sponge Polyketide Callystatin A

  摘要：

  A C13-22 syn,syn,syn,syn-stereopentad precursor of the cytotoxic polyketide callystatin A has been prepared. The synthesis involved BF3-promoted addition of the (M)-allenylstannane 28 to the alpha-methyl-beta-OTBS aldehyde 8 to afford the syn,syn adduct homopropargylic alcohol 29. Protection as the cyclic anisylidene acetal 31 and reduction of the acetylenic triple bond with Red-Al gave the (E)-allylic alcohol 32. This was subjected to Sharpless asymmetric epoxidation and subsequent treatment with an ethylcopper reagent to yield diol 34; hydrogenolysis of the derived tosylate 37 with LiBEt3H afforded 38. Acetal hydrogenolysis with DIBAl-H and oxidation yielded aldehyde 40 which was subjected to Horner-Emmons homologation to afford ester 41. This ester was converted to ester 44, an intermediate in the Kobayashi synthesis, with which it was found to be identical.

  DOI：

  10.1021/jo9902143

文献信息

• SYNTHESIS OF HDAC INHIBITORS: TRICHOSTATIN A AND ANALOGUES
  申请人：Helquist Paul

  公开号：US20110237832A1

  公开（公告）日：2011-09-29

  Embodiments herein relate to histone deacetylaces (HDACs) and HDAC inhibitors, such as trichostatin A (TSA) and TSA analogues. Embodiments provide simple methods of synthesizing TSA and TSA analogues. These methods provide routes of synthesis of TSA and TSA analogues that enable the production of the HDAC inhibitors at lower cost and in greater quantities than previously were available.

  本文涉及组蛋白去乙酰化酶（HDACs）和HDAC抑制剂，如三氯乙酸（TSA）及其类似物。实施例提供了合成TSA和TSA类似物的简单方法。这些方法提供了合成TSA和TSA类似物的途径，使得生产HDAC抑制剂的成本更低、数量更大，比以往更容易获得。
• Stereoselective Synthesis of Stereotriad Subunits of Polyketides through Additions of Nonracemic Allenylsilanes to <i>(R</i>)- and <i>(S</i>)-2-Methyl-3-oxygenated Propanals
  作者：James A. Marshall、Karin Maxson

  DOI：10.1021/jo991543y

  日期：2000.1.1
• Synthesis of a <i>syn,syn,syn,syn</i>-Stereopentad Precursor of the Marine Sponge Polyketide Callystatin A
  作者：James A. Marshall、Russell N. Fitzgerald

  DOI：10.1021/jo9902143

  日期：1999.6.1

  A C13-22 syn,syn,syn,syn-stereopentad precursor of the cytotoxic polyketide callystatin A has been prepared. The synthesis involved BF3-promoted addition of the (M)-allenylstannane 28 to the alpha-methyl-beta-OTBS aldehyde 8 to afford the syn,syn adduct homopropargylic alcohol 29. Protection as the cyclic anisylidene acetal 31 and reduction of the acetylenic triple bond with Red-Al gave the (E)-allylic alcohol 32. This was subjected to Sharpless asymmetric epoxidation and subsequent treatment with an ethylcopper reagent to yield diol 34; hydrogenolysis of the derived tosylate 37 with LiBEt3H afforded 38. Acetal hydrogenolysis with DIBAl-H and oxidation yielded aldehyde 40 which was subjected to Horner-Emmons homologation to afford ester 41. This ester was converted to ester 44, an intermediate in the Kobayashi synthesis, with which it was found to be identical.