(2S,3S,4S,5R,6S)-4,5-Diacetoxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 870192-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-4,5-Diacetoxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (methyl 2,3-di-O-acetyl-α-D-glucopyranosid)uronate
• CAS: 870192-80-6
• 化学式: C₁₂H₁₈O₉
• 分子量: 306.27
• InChiKey: XJRFTPMNRGKWKW-GBVMLCMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.24
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-4,5-Diacetoxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 4 A molecular sieve 、 四丁基氟化铵 、 三乙基硅基三氟甲磺酸酯 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid

  摘要：

  A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.019
• 作为产物：
  描述：

  methyl 2,3-di-O-acetyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 溶剂黄146 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 生成 (2S,3S,4S,5R,6S)-4,5-Diacetoxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid

  摘要：

  A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.019

文献信息

• 4-(tert-Butyldiphenylsilyloxy)-2,2-dimethylbutanoyl: An Easily Removable Pivaloyl-Type Protecting Group with High Orthogonality
  作者：Ming Li、Qishuai Li、Yong Su、Zhi Qiao、Jianjun Wang、Peng Wang、Sumei Ren、Ni Song

  DOI：10.1055/a-1751-1225

  日期：2022.6

  Protecting groups play multiple and vital roles during the synthesis of carbohydrates and other natural products. We herein report the installation and orthogonal cleavage, under mild conditions, of a 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutanoyl (BDMB) group as a sterically hindered pivaloyl-type hydroxy protecting group. The compatibility of this substituent with the removal of other protecting

  保护基团在碳水化合物和其他天然产物的合成过程中发挥着多重和重要的作用。我们在此报告了在温和条件下安装和正交裂解 4-(叔丁基二苯基甲硅烷氧基)-2,2-二甲基丁酰基 (BDMB) 基团作为空间受阻的新戊酰基型羟基保护基团。还研究了该取代基与去除其他保护基团的相容性。由于其有利的特性，预计 BDMB 可作为一种有价值的羟基掩蔽剂。