ethyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside | 1004771-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 2,3-di-O-acetyl-6-O-benzoyl-β-D-thioglucopyranose；ethyl 2,3-di-O-acetyl-6-O-benzoyl-1-deoxy-1-thio-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-ethylsulfanyl-3-hydroxyoxan-2-yl]methyl benzoate
• CAS: 1004771-40-7
• 化学式: C₁₉H₂₄O₈S
• 分子量: 412.461
• InChiKey: JELUHWYCERHXSP-ILYVXUQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside 、 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 perchloric acid adsorbed on silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethyl (2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-1-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Convergent synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14

  摘要：

  An efficient synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14 is reported. A one-pot, two step iterative glycosylation and [3+2] block synthetic strategy have been adopted for the construction of the pentasaccharide derivative 11, which was then transformed into target compound 1 after a series of functional group transformations. The primary hydroxyl group has been selectively oxidized to a carboxylic acid functionality without affecting the secondary hydroxyl groups. HClO4-SiO2 has been used as a solid acid substitute in all glycosylation and functional group transformations. The yields were excellent in all glycosylation steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.004
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 ethyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  可见光介导的氧化脱苄基作用使得能够使用苄基醚作为临时保护基团

  摘要：

  通过催化氢解或 Birch 还原裂解苄基醚存在官能团相容性差的问题，限制了它们作为保护基团的用途。本文公开的可见光介导的脱苄基作用使苄基醚成为临时保护基团，从而实现新的正交保护策略。使用 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 作为化学计量或催化光氧化剂，可以在叠氮化物、烯烃和炔烃存在下裂解苄基醚。在连续流动中，反应时间可以从几小时缩短至几分钟。

  DOI：

  10.1021/acs.orglett.0c04026

文献信息

• Synthesis of flaccidoside II, a bidesmosidic triterpene saponin isolated from Chinese folk medicine Di Wu
  作者：Shuihong Cheng、Yuguo Du、Feihong Bing、Guobin Zhang

  DOI：10.1016/j.carres.2007.11.015

  日期：2008.2

  A total synthesis of flaccidoside II, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyloleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside, isolated from Chinese folk medicine Di Wu, has been accomplished from building blocks isopropyl 2-O-acetyl-3,4-di-O-benzoyl-1-thio-beta-D-xylopyranoside, 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate

  总黄酮苷II，3-O-α-L-鼠李吡喃糖基-（1-> 2）-β-D-吡喃并吡喃基果酸28-O-α-L-鼠李吡喃糖基-（1-> 4）-β -D-吡喃葡萄糖基-（1-> 6）-β-D-吡喃葡萄糖苷是从异丙基2-O-乙酰基-3,4-二-O-苯甲酰基-的结构单元中分离而来的1-硫代-β-D-吡喃吡喃糖苷，2,3,4-三-O-苯甲酰基-α-L-鼠李吡喃糖基三氯乙酰亚胺酸酯，齐墩果酸三苯甲基酯，2,3-二-O-乙酰基-6-O-苯甲酰基乙酯-1-硫代-β-D-吡喃葡萄糖苷和4-甲氧基苯基2,3,4-三-O-乙酰基-β-D-吡喃葡萄糖苷。使用部分保护的硫糖基供体可大大简化目标皂苷的合成。
• Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu
  作者：Xing Huang、Shuihong Cheng、Yuguo Du、Feihong Bing

  DOI：10.1016/j.carres.2009.04.005

  日期：2009.7

  3,28-Di-O-rhamnosylated oleanolic acid saponins, mimicking components of Chinese folk medicine Di Wu, have been designed and synthesized. one-pot glycosylation and 'inverse procedure' technologies have been applied thus significantly simplifying the preparation of desired saponins. The cytotoxic activity of compounds 3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (3), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl- (1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (4), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl] ester (5), and 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[6-O-(alpha-L-rhamnopyranosyl)hexyl] ester (6) was preliminarily evaluated against HL-60 human promyelocytic leukemia cells. The natural saponin 3 and designed saponin 4 exhibited comparable moderate cytotoxic activity under our testing conditions. (C) 2009 Elsevier Ltd. All rights reserved.