[(2R,3R,4S,5S)-3-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-3-[(2R,3S,4R,5R)-4-benzoyloxy-5-(benzoyloxymethyl)-3-(2-chloroacetyl)oxyoxolan-2-yl]oxy-5-[[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-(2-chloroethoxy)oxolan-2-yl]methoxy]oxolan-2-yl]methoxy]-4-(2-chloroacetyl)oxyoxolan-2-yl]methyl benzoate | 1289100-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5S)-3-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-3-[(2R,3S,4R,5R)-4-benzoyloxy-5-(benzoyloxymethyl)-3-(2-chloroacetyl)oxyoxolan-2-yl]oxy-5-[[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-(2-chloroethoxy)oxolan-2-yl]methoxy]oxolan-2-yl]methoxy]-4-(2-chloroacetyl)oxyoxolan-2-yl]methyl benzoate
• CAS: 1289100-92-0
• 化学式: C₇₅H₆₇Cl₃O₂₆
• 分子量: 1490.7
• InChiKey: ZMXVOWOTTSMHAW-ZDBVJPROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  104
• 可旋转键数：
  40
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  311
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S)-3-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-3-[(2R,3S,4R,5R)-4-benzoyloxy-5-(benzoyloxymethyl)-3-(2-chloroacetyl)oxyoxolan-2-yl]oxy-5-[[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-(2-chloroethoxy)oxolan-2-yl]methoxy]oxolan-2-yl]methoxy]-4-(2-chloroacetyl)oxyoxolan-2-yl]methyl benzoate 在 吡啶 、 水 作用下， 反应 3.5h， 以85%的产率得到2-chloroethyl 2,3-di-O-benzoyl-5-O-[2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranosyl]-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of hexasaccharide fragment of lipoarabonomannan from Mycobacteria: advantages of the benzyl-free approach

  摘要：

  通过三种不同的途径合成了空间支链六阿拉伯呋喃糖苷，该物质与分枝杆菌脂阿拉伯甘露聚糖和阿拉伯半乳聚糖的末端片段相对应。仅涉及酰基和硅基保护基团（不含苄基的方法）的合成方案可以减少脱保护步骤，提高总产量，并在合成结束时保留叠氮基。

  DOI：

  10.1007/s11172-015-0992-5
• 作为产物：
  描述：

  在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到[(2R,3R,4S,5S)-3-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-3-[(2R,3S,4R,5R)-4-benzoyloxy-5-(benzoyloxymethyl)-3-(2-chloroacetyl)oxyoxolan-2-yl]oxy-5-[[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-(2-chloroethoxy)oxolan-2-yl]methoxy]oxolan-2-yl]methoxy]-4-(2-chloroacetyl)oxyoxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Formation of orthoester-linked d-arabinofuranose oligosaccharides and their isomerization into the corresponding glycosides

  摘要：

  Orthoester-linked D-arabinofuranose oligosaccharides were isolated in high yield for the first time via glycosylations with 2-O-chloroacetyl-substituded D-arabinofuranose thioglycosides promoted by NIS-AgOTf in the presence of 4 A molecular sieves in CH2Cl2. These orthoesters can be rearranged into the isomeric glycosidically-linked oligosaccharides by treatment with TMSOTf in CH2Cl2, or in situ by extension of the reaction time. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.019

文献信息

• Synthesis of covalent conjugates of hexaarabinofuranoside with proteins and their testing as antigens for serodiagnosis of tuberculosis
  作者：P. I. Abronina、N. M. Podvalnyy、T. M. Mel’nikova、A. I. Zinin、K. G. Fedina、V. V. Kachala、V. I. Torgov、L. O. Kononov、E. A. Panfertsev、E. V. Baranova、V. V. Mochalov、V. I. Dyatlova、S. F. Biketov

  DOI：10.1007/s11172-010-0397-4

  日期：2010.12
• Formation of orthoester-linked d-arabinofuranose oligosaccharides and their isomerization into the corresponding glycosides
  作者：Polina I. Abronina、Sergey L. Sedinkin、Nikita M. Podvalnyy、Ksenia G. Fedina、Alexander I. Zinin、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.tetlet.2011.02.019

  日期：2011.4

  Orthoester-linked D-arabinofuranose oligosaccharides were isolated in high yield for the first time via glycosylations with 2-O-chloroacetyl-substituded D-arabinofuranose thioglycosides promoted by NIS-AgOTf in the presence of 4 A molecular sieves in CH2Cl2. These orthoesters can be rearranged into the isomeric glycosidically-linked oligosaccharides by treatment with TMSOTf in CH2Cl2, or in situ by extension of the reaction time. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of hexasaccharide fragment of lipoarabonomannan from Mycobacteria: advantages of the benzyl-free approach
  作者：N. M. Podvalnyy、P. I. Abronina、K. G. Fedina、N. N. Kondakov、A. I. Zinin、A. O. Chizhov、V. I. Torgov、V. V. Kachala、L. O. Kononov

  DOI：10.1007/s11172-015-0992-5

  日期：2015.5

  Spacered branched hexaarabinofuranoside, which corresponds to the terminal fragment of mycobacterial lipoarabinomannan and arabinogalactan, was synthesized via three different routes. Synthetic scheme which involved only acyl and silyl protective groups (benzyl-free approach) allows one to reduce the number of deprotection steps, enhance the overall yield, and keep the azido group until the end of the synthesis.

  通过三种不同的途径合成了空间支链六阿拉伯呋喃糖苷，该物质与分枝杆菌脂阿拉伯甘露聚糖和阿拉伯半乳聚糖的末端片段相对应。仅涉及酰基和硅基保护基团（不含苄基的方法）的合成方案可以减少脱保护步骤，提高总产量，并在合成结束时保留叠氮基。