ethyl 3,4-di-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside | 606934-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4-di-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-ethylsulfanyl-6-methyloxan-3-ol
• CAS: 606934-66-1
• 化学式: C₂₀H₄₄O₄SSi₂
• 分子量: 436.804
• InChiKey: CHGDJJSIPFBNLX-IECFSIQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 ethyl 3,4-di-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside 在 吡啶 作用下， 反应 10.0h， 以20%的产率得到ethyl 2-O-acetyl-3,4-di-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of 2-chloro-4-nitrophenyl α-l-fucopyranoside: a substrate for α-l-fucosidase (AFU)

  摘要：

  An effective method to prepare the substrate of alpha-L-fucosidase (AFU) is described. Ethyl 1-thiofucoside with a free 2-OH group was used as the glycosyl donor, and there was found no self-condensed side product. The use of the HF . pyridine reagent to remove the silyl protecting group in the last step afforded a target molecule of high purity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00244-1
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 ethyl 1-thio-β-L-fucopyranoside 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以78%的产率得到ethyl 3,4-di-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of 2-chloro-4-nitrophenyl α-l-fucopyranoside: a substrate for α-l-fucosidase (AFU)

  摘要：

  An effective method to prepare the substrate of alpha-L-fucosidase (AFU) is described. Ethyl 1-thiofucoside with a free 2-OH group was used as the glycosyl donor, and there was found no self-condensed side product. The use of the HF . pyridine reagent to remove the silyl protecting group in the last step afforded a target molecule of high purity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00244-1

文献信息

• Synthesis of new, potent avermectin-like insecticidal agents
  作者：Lijun Wei、Guohua Wei、Houcheng Zhang、Peng G. Wang、Yuguo Du

  DOI：10.1016/j.carres.2005.04.019

  日期：2005.7

  4'-Modified avermectin derivatives were designed and synthesized. Some of the new synthetic compounds showed excellent in vivo bioactivity against cabbage larvae when compared to commercially available avermectin B-1a. In this synthesis, uncommon thioglycosyl sugar donors, prepared from the hydrolysis of natural antibiotics, proved compatible with sugar-macrolide synthesis in the presence of N-iodosuccinimide (NIS) or I-2 in N-methylpyrrolidone at room temperature. (c) 2005 Published by Elsevier Ltd.
• Synthesis of 2-chloro-4-nitrophenyl α-l-fucopyranoside: a substrate for α-l-fucosidase (AFU)
  作者：Guofeng Gu、Yuguo Du、Hongyan Hu、Cheng Jin

  DOI：10.1016/s0008-6215(03)00244-1

  日期：2003.7

  An effective method to prepare the substrate of alpha-L-fucosidase (AFU) is described. Ethyl 1-thiofucoside with a free 2-OH group was used as the glycosyl donor, and there was found no self-condensed side product. The use of the HF . pyridine reagent to remove the silyl protecting group in the last step afforded a target molecule of high purity. (C) 2003 Elsevier Ltd. All rights reserved.