4-O-(tert-butyldimethylsilyl)-2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal | 1555449-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(tert-butyldimethylsilyl)-2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal
• CAS: 1555449-25-6
• 化学式: C₂₂H₄₄O₅S₂Si
• 分子量: 480.806
• InChiKey: FAOCXVZYANSEHM-ZJPYXAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-O-(tert-butyldimethylsilyl)-2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal 在 N-溴代丁二酰亚胺(NBS) 、 2,6-二叔丁基-4-甲基吡啶 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.5h， 生成 4-O-(tert-butyldimethylsilyl)-2,3:5,6-di-O-isopropylidene-D-glucitol-1-yl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-methoxybenzyl)-β-D-mannopyranoside
  参考文献：
  名称：

  Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry

  摘要：

  Five alditol analogs 1b-1f of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, were synthesized by employing a stereoselective beta-mannosylation of appropriately protected mannose with five hexitols with different stereochemistry, and their potential on modulating Ca2+ signaling were evaluated. All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.052
• 作为产物：
  描述：

  D-葡萄糖 在 2,6-二甲基吡啶 、 盐酸 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.5h， 生成 4-O-(tert-butyldimethylsilyl)-2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal
  参考文献：
  名称：

  Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry

  摘要：

  Five alditol analogs 1b-1f of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, were synthesized by employing a stereoselective beta-mannosylation of appropriately protected mannose with five hexitols with different stereochemistry, and their potential on modulating Ca2+ signaling were evaluated. All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.052

文献信息

• Synthesis of Symmetrical Dodeco‐6,7‐diuloses
  作者：Marius Bayer、Simon Stocker、Cäcilia Maichle‐Mössmer、Thomas Ziegler

  DOI：10.1002/ejoc.202000615

  日期：2020.8.2

  Four different synthetic strategies towards dodeco‐6,7‐diuloses, which are structurally related to naturally occurring Peltalosa, are presented. Furthermore, detailed NMR spectroscopic investigations of these felxible, bis‐hemiacetalic compounds indicate a tendency to form preferred isomers.

  提出了针对dodeco-6,7-dioseoses的四种不同合成策略，这些策略在结构上与天然存在的Peltalosa有关。此外，对这些易燃的双半缩醛化合物的详细NMR光谱研究表明，有形成优选异构体的趋势。