3-O-acetyl-5-O-(allylthiocarbonyl)-6-chloro-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose | 1195937-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3-O-acetyl-5-O-(allylthiocarbonyl)-6-chloro-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
• CAS: 1195937-67-7
• 化学式: C₁₅H₂₁ClO₇S
• 分子量: 380.847
• InChiKey: GZQZJQCMSIJHCJ-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  3-O-Acetyl-1,2-O-isopropyliden-α-D-glucofuranose-5,6-thionocarbonat 、 3-氯丙烯 反应 0.5h， 以40%的产率得到3-O-acetyl-5-O-(allylthiocarbonyl)-6-chloro-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
  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