6-O-(tert-butyldiphenylsilyl)-2,3:4,5-di-O-isopropylidene-D-galactitol | 1555448-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(tert-butyldiphenylsilyl)-2,3:4,5-di-O-isopropylidene-D-galactitol
• CAS: 1555448-89-9
• 化学式: C₂₈H₄₀O₆Si
• 分子量: 500.707
• InChiKey: IMZOCDJAOGEMAU-LIONHTAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-O-(tert-butyldiphenylsilyl)-2,3:4,5-di-O-isopropylidene-D-galactitol 在 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 palladium on activated charcoal 、 四丁基氟化铵 、 氢气 、 trifluoromethanesulfonic acid anhydride 、 N,N-二异丙基乙胺 、 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 、 乙酸乙酯 为溶剂， 反应 42.17h， 生成 2,3:4,5-di-O-isopropylidene-1-methoxymethyl-D-galactitol-6-yl 2-O-octanoyl-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-吡喃葡萄糖 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以81%的产率得到6-O-(tert-butyldiphenylsilyl)-2,3:4,5-di-O-isopropylidene-D-galactitol
  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