(S)-1-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol | 73209-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol
• 英文别名: (1S)-1-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 73209-96-8
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: DSFHQKBBQMLHSW-LYFYHCNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.15
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol 在 sodium periodate 作用下， 以 水 为溶剂， 生成 2,3-O-isopropylidene-L-erythrofuranose
  参考文献：
  名称：

  A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH

  摘要：

  A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.069
• 作为产物：
  描述：

  L-(+)-arabinose 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-1-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol
  参考文献：
  名称：

  A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH

  摘要：

  A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.069