S-3,3-dimethoxypropyl methanethiosulfonate | 886733-92-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: S-3,3-dimethoxypropyl methanethiosulfonate
• 英文别名: 3,3-dimethoxypropyl methanethiosulfonate；1,1-Dimethoxy-3-methylsulfonylsulfanylpropane
• CAS: 886733-92-2
• 化学式: C₆H₁₄O₄S₂
• 分子量: 214.307
• InChiKey: KDTZNFBABHAGIB-UHFFFAOYSA-N

物化性质

• 沸点：
  341.8±32.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-3,3-dimethoxypropyl methanethiosulfonate 在 titanium(IV) isopropylate 、 六甲基磷酰三胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (R,E)-benzyl 2-(3,3-dimethoxypropylthio)-2,4-dimethylhexa-3,5-dienoate
  参考文献：
  名称：

  Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

  摘要：

  Starting with commercially available tiglic aldehyde, the title synthesis was achieved by employing deconjugative asymmetric alpha-sulfenylation of the chiral 3-(alpha,beta,gamma,delta-unsaturated acyl)-2-oxazolidinone with a methanethiosulfonate as a key step. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.058
• 作为产物：
  描述：

  1,2-bis(3,3-dimethoxypropyl)disulfane 、 sodium methansulfinate 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到S-3,3-dimethoxypropyl methanethiosulfonate
  参考文献：
  名称：

  硫菌霉素及其3-脱甲基衍生物对映体对的高效合成和生物活性

  摘要：

  通过使用手性3-（α，β，γ，δ-不饱和酰基）恶唑烷-2-酮与3,3-二甲氧基丙基甲硫代磺酸盐的键合不对称α-亚磺酰基化作为关键步骤来实现标题的总合成。从使用标题化合物进行的生物学活性测定中，似乎表明，不仅通过改变C 3位的取代基，而且通过改变C的绝对构型，可以清楚地分离体外的抗菌和哺乳动物I型FAS抑制活性。5位，并且非天然的（S）-（-）-3-脱甲基硫基催乳素及其同源物可以用作选择性的哺乳动物I型FAS抑制剂。

  DOI：

  10.1016/j.tet.2009.01.054

文献信息

• Synthesis and biological activity of enantiomeric pairs of 5-vinylthiolactomycin congeners
  作者：Kohei Ohata、Shiro Terashima

  DOI：10.1016/j.bmcl.2007.04.067

  日期：2007.7

  prepared, it appeared evident that in vitro antibacterial and mammalian type I FAS inhibitory activity of thiolactomycin congeners can be cleanly separated by changing not only the structure but also the absolute configuration of the side chain at the C(5)-position. These studies led us to explore (S)-3-demethyl-5-(pent-1-enyl)thiolactomycin derivative [(S)-4-hydroxy-5-methyl-5-(pent-1-enyl)-5H-thiophen-2-one]

  通过使用我们先前探索的用于合成硫菌丝霉素及其3-脱甲基衍生物的对映体对的有效合成路线，合成了十二个5-乙烯基硫基乳酸霉素同系物的对映体对。从使用获得的同源物以及先前制备的对映体对的硫菌霉素及其3-脱甲基衍生物进行的生物活性分析，似乎可以看出，通过不改变不仅是侧链在C（5）位置的结构而且是绝对构型。
• Synthesis and Biological Activity of Enantiomeric Pairs of 5-(Alk-2-enyl)thiolactomycin and 5-[(E)-Cycloalk-2-enylidenemethyl]thiolactomycin Congeners
  作者：Kohei Ohata、Shiro Terashima

  DOI：10.1248/cpb.57.920

  日期：——

  The title compounds were synthesized by the efficient route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. These studies were carried out to prove the flexibility of the previously explored synthetic route to natural thiolactomycin (TLM) 1 and to examine the structure–activity relationship on the 5-position of 1. While all of the synthesized congeners lacked in vitro antibacterial activity, these studies led us to find 5-(alk-2-enyl)-TLM (ent-4d) which exhibits mammalian type I fatty acid synthase (FAS) inhibitory activity equal to that of C75, a potent inhibitor reported previously. It was also found that 5-[(E)-cycloalk-2-enylidenemethyl]-TLM (ent-5c) exhibited slightly less potent mammalian type I FAS inhibitory activity than C75.

  标题化合物是通过之前探索的合成硫代霉素对映体及其 3-去甲基衍生物的高效路线合成的。虽然所有合成的同系物都缺乏体外抗菌活性，但这些研究使我们发现了 5-(alk-2-enyl)-TLM（ent-4d），它对哺乳动物 I 型脂肪酸合成酶（FAS）的抑制活性与之前报道的强效抑制剂 C75 相当。研究还发现，5-[(E)-环烷-2-亚烯基甲基]-TLM（ent-5c）对哺乳动物 I 型脂肪酸合成酶的抑制活性略低于 C75。
• Synthesis and biological activity of enantiomeric pairs of 5-[(E)-cycloalk-2-enylidenemethyl]thiolactomycin congeners
  作者：Kohei Ohata、Shiro Terashima

  DOI：10.1016/j.bmcl.2008.08.103

  日期：2008.10

  The title congeners were synthesized by employing our efficient synthetic route previously explored for preparing enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. While all the synthesized congeners lacked in vitro antibacterial activity, some of the congeners bearing an (E)-cyclohept-2-enylidenemethyl or an (E)-cyclooct-2-enylidenemethyl group were found to exhibit more potent type

  通过使用我们先前探索的用于制备硫菌霉素及其3-脱甲基衍生物的对映异构体对的有效合成途径，合成了标题同源物。虽然所有合成的同类物均缺乏体外抗菌活性，但发现一些带有（E）-环庚-2-烯基甲基或（E）-环辛-2-烯基甲基的同类物比Is FAS具有更强的抑制活性（S）-3-demethylthiolactomycin具有非天然构型。
• Efficient synthesis and biological activity of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative
  作者：Kohei Ohata、Shiro Terashima

  DOI：10.1016/j.tet.2009.01.054

  日期：2009.3

  The title total synthesis was achieved by employing deconjugative asymmetric α-sulfenylation of the chiral 3-(α,β,γ,δ-unsaturated acyl)oxazolidin-2-one with a 3,3-dimethoxypropyl methanethiosulfonate as a key step. From the biological activity assay carried out using the title compounds, it appeared evident that in vitro antibacterial and mammalian type I FAS inhibitory activity can be cleanly separated

  通过使用手性3-（α，β，γ，δ-不饱和酰基）恶唑烷-2-酮与3,3-二甲氧基丙基甲硫代磺酸盐的键合不对称α-亚磺酰基化作为关键步骤来实现标题的总合成。从使用标题化合物进行的生物学活性测定中，似乎表明，不仅通过改变C 3位的取代基，而且通过改变C的绝对构型，可以清楚地分离体外的抗菌和哺乳动物I型FAS抑制活性。5位，并且非天然的（S）-（-）-3-脱甲基硫基催乳素及其同源物可以用作选择性的哺乳动物I型FAS抑制剂。
• Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative
  作者：Kohei Ohata、Shiro Terashima

  DOI：10.1016/j.tetlet.2006.02.058

  日期：2006.4

  Starting with commercially available tiglic aldehyde, the title synthesis was achieved by employing deconjugative asymmetric alpha-sulfenylation of the chiral 3-(alpha,beta,gamma,delta-unsaturated acyl)-2-oxazolidinone with a methanethiosulfonate as a key step. (c) 2006 Elsevier Ltd. All rights reserved.