Methyl-(6-S-acetyl-2,3-O-isopropyliden-6-thia-β-D-ribofuranosid) | 15354-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-(6-S-acetyl-2,3-O-isopropyliden-6-thia-β-D-ribofuranosid)
• 英文别名: Methyl-5-S-acetyl-2,3-O-isopropyliden-5-thio-β-D-ribofuranosid；S-[[(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl] ethanethioate
• CAS: 15354-43-5
• 化学式: C₁₁H₁₈O₅S
• 分子量: 262.327
• InChiKey: HHLZURZZYHAHRW-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl-(6-S-acetyl-2,3-O-isopropyliden-6-thia-β-D-ribofuranosid) 在 sodium tetrahydroborate 、 硫酸 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 5-thio-D-ribopyranose
  参考文献：
  名称：

  Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-d-ribopyranosides as well as their 2-deoxy and 2,3-dideoxy derivatives possessing antithrombotic activity

  摘要：

  1,2,3,4-Tetra-O-acetyl-5-thio-D-ribopyranose as well as its 1-bromide were used as donors in the reaction with 4-cyano- and 4-nitrobenzenethiol to give the corresponding thiogrycosides in different anomeric ratios depending on the reaction conditions. Zemplen deacetylation afforded 4-cyanophenyl as well as 4-nitrophenyl 1,5-dithio-alpha- and beta-D-ribopyranosides, respectively. 1,3,4-Tri-O-acetyl-2-deoxy-5-thio-D-erythro-pentopyranose was synthesized from methyl 2-deoxy-D-erythro-pentofuranoside and was coupled with 4-cyano- and 4-nitrobenzenethiol to give anomeric mixtures from which 4-cyanophenyl as well. as 4-nitrophenyl. 1,5-dithio-beta-D-erythro-pentopyranosides were isolated after deacetylation. 1,4-Di-O-acetyl-2,3-dideoxy-5-thio-D-glycero-pentopyranose was obtained starting from 1,2;5,6-di-O-isopropylidene-D-mannitol and used as the donor in the glycosylation reaction with 4-cyano- and 4-nitrobenzenethiol. The resulting anomeric mixtures were separated to give, after deacetylation, 4-cyanophenyl as well as 4-nitrophenyl 2,3-dideoxy-1,5-dithio-beta-D-glycero-pentopyranosides. All of these thioglycosides showed significant antithrombotic activity on rats after oral administration. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00175-5
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl-(6-S-acetyl-2,3-O-isopropyliden-6-thia-β-D-ribofuranosid)
  参考文献：
  名称：

  含有衍生自碳水化合物的配体的新型金（I）和金（III）配合物的合成，表征，细胞毒性和抗结核活性。

  摘要：

  合成了含有D-半乳糖，D-核糖和D-葡萄糖基-1,5-内酯衍生物的新型金（I）和金（III）配合物，并通过IR，（1）H和（13）C进行了表征NMR，高分辨率质谱和循环伏安法。体外评估了这些化合物对三种类型的肿瘤细胞的细胞毒性：宫颈癌（HeLa）乳腺腺癌（MCF-7）和胶质母细胞瘤（MO59J），以及一种非肿瘤细胞系：人肺成纤维细胞（GM07492A）。评估它们的抗结核活性，并以μg/ mL的最低抑菌浓度（MIC90）表示。通常，金（I）配合物比金（III）配合物更具活性，例如，金（I）配合物（1）的毒性是金（III）配合物（8）的约8.8倍和细胞毒性的7.6倍。 MO59J和MCF-7电池。核糖和烷基膦衍生物的配合物比半乳糖和芳基膦的配合物更具活性。噻唑烷环的存在不能改善细胞毒性。细胞毒性活性的研究表明，金（I）复合物具有有效的抗肿瘤活性，在所有测试的肿瘤细胞系中比顺铂更具活性。即使与一

  DOI：

  10.1007/s10534-015-9870-8