[(3aR,5S,6S,6aR)-2,2-dimethyl-5-[(1S)-2-prop-2-enylsulfanyl-1-prop-2-enylsulfanylcarbonyloxyethyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate | 1195937-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,5S,6S,6aR)-2,2-dimethyl-5-[(1S)-2-prop-2-enylsulfanyl-1-prop-2-enylsulfanylcarbonyloxyethyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 1195937-72-4
• 化学式: C₁₈H₂₆O₇S₂
• 分子量: 418.532
• InChiKey: PGCFZIWYUDOBIZ-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(3aR,5S,6S,6aR)-2,2-dimethyl-5-[(1S)-2-prop-2-enylsulfanyl-1-prop-2-enylsulfanylcarbonyloxyethyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到C₁₆H₂₂O₇S₂
  参考文献：
  名称：

  Stereoselective synthesis of new glycooxathiecinone using vic-cyclic thionocarbonate haloalkylation and ring closing metathesis as key steps

  摘要：

  Herein, we describe the first glycoconjugate macrocyclic thiolcarbonate namely (Z)-10(S)-[3'-O-acetyl-1',2'-O-isopropylidene-4'-deoxy-D-erythtofuranose]-4,7,9-trihydro-10H-8-thia-1,3-oxathiecin-2-one (17a) using a strategy based on two key steps synthesis: (i) a haloalkylation of vic-diol via their cyclic thionocarbonate derivatives; (ii) a macrocyclisation using ring closing metathesis reaction. Detailed here is a newly developed extension of vic-diol halogenation via the cyclic thionocarbonate function but using a range of alkyl halides other than the customarily used Mel. For example, with 1,2-O-isopropylidene-5,6-O-thionocarbonate-D-glucose (1) and allyl bromide, the 5-allylthiolcarbonate-6-bromo-6-deoxy-D-glucose derivative 6 was obtained in good yield. The later submitted to 6-allythioetherification and ring closing metathesis (RCM) with Grubbs second generation gave stereoselectively the target oxathiecinone 17a in 75% yield for the RCM step. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.016
• 作为产物：
  描述：

  烯丙硫醇 、 3-O-acetyl-5-O-(allylthiocarbonyl)-6-bromo-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 caesium carbonate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.25h， 以60%的产率得到[(3aR,5S,6S,6aR)-2,2-dimethyl-5-[(1S)-2-prop-2-enylsulfanyl-1-prop-2-enylsulfanylcarbonyloxyethyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
  参考文献：
  名称：

  Stereoselective synthesis of new glycooxathiecinone using vic-cyclic thionocarbonate haloalkylation and ring closing metathesis as key steps

  摘要：

  Herein, we describe the first glycoconjugate macrocyclic thiolcarbonate namely (Z)-10(S)-[3'-O-acetyl-1',2'-O-isopropylidene-4'-deoxy-D-erythtofuranose]-4,7,9-trihydro-10H-8-thia-1,3-oxathiecin-2-one (17a) using a strategy based on two key steps synthesis: (i) a haloalkylation of vic-diol via their cyclic thionocarbonate derivatives; (ii) a macrocyclisation using ring closing metathesis reaction. Detailed here is a newly developed extension of vic-diol halogenation via the cyclic thionocarbonate function but using a range of alkyl halides other than the customarily used Mel. For example, with 1,2-O-isopropylidene-5,6-O-thionocarbonate-D-glucose (1) and allyl bromide, the 5-allylthiolcarbonate-6-bromo-6-deoxy-D-glucose derivative 6 was obtained in good yield. The later submitted to 6-allythioetherification and ring closing metathesis (RCM) with Grubbs second generation gave stereoselectively the target oxathiecinone 17a in 75% yield for the RCM step. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.016