[(3aR,5S,6S,6aR)-5-[(1S)-1-(2-amino-2-oxoethyl)sulfanylcarbonyloxy-2-iodoethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate | 1195937-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [(3aR,5S,6S,6aR)-5-[(1S)-1-(2-amino-2-oxoethyl)sulfanylcarbonyloxy-2-iodoethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 1195937-71-3
• 化学式: C₁₄H₂₀INO₈S
• 分子量: 489.285
• InChiKey: HWAPJGYAPCUFHS-DVYMNCLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-O-Acetyl-1,2-O-isopropyliden-α-D-glucofuranose-5,6-thionocarbonat 、 2-碘乙酰胺 以 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到[(3aR,5S,6S,6aR)-5-[(1S)-1-(2-amino-2-oxoethyl)sulfanylcarbonyloxy-2-iodoethyl]-2,2-dimethyl-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