2'-(benzyloxycarbonyl)benzyl 2-O-(tert-butyl(dimethyl)silyl)-5,6-O-isopropylidene-β-D-galactofuranoside | 911371-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(benzyloxycarbonyl)benzyl 2-O-(tert-butyl(dimethyl)silyl)-5,6-O-isopropylidene-β-D-galactofuranoside
• 英文别名: benzyl 2-[[(2R,3R,4S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxyoxolan-2-yl]oxymethyl]benzoate
• CAS: 911371-44-3
• 化学式: C₃₀H₄₂O₈Si
• 分子量: 558.744
• InChiKey: YVACFAOGXKQHMG-BZTMQRDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-(benzyloxycarbonyl)benzyl 2-O-(tert-butyl(dimethyl)silyl)-5,6-O-isopropylidene-β-D-galactofuranoside 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2'-(benzyloxycarbonyl)benzyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranoside
  参考文献：
  名称：

  Total Synthesis of Agelagalastatin

  摘要：

  The total synthesis of agelagalastatin, an antineoplastic glycosphingolipid, has been achieved. The synthesis involved an alpha-selective glycosylation of the ceramide moiety with the trisaccharide fluoride. The trisaccharide component was constructed employing the CB glycoside method which permitted a completely alpha-stereoselective galactofuranosylation.

  DOI：

  10.1021/ol061444o
• 作为产物：
  描述：

  2'-(benzyloxycarbonyl)benzyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranoside 在 咪唑 、 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2'-(benzyloxycarbonyl)benzyl 2-O-(tert-butyl(dimethyl)silyl)-5,6-O-isopropylidene-β-D-galactofuranoside
  参考文献：
  名称：

  Total Synthesis of Agelagalastatin

  摘要：

  The total synthesis of agelagalastatin, an antineoplastic glycosphingolipid, has been achieved. The synthesis involved an alpha-selective glycosylation of the ceramide moiety with the trisaccharide fluoride. The trisaccharide component was constructed employing the CB glycoside method which permitted a completely alpha-stereoselective galactofuranosylation.

  DOI：

  10.1021/ol061444o

文献信息

• Stereoselective α-galactofuranosylation and synthesis of di- and tetrasaccharide subunits of cell wall polysaccharides of Talaromyces flavus
  作者：Ju Yuel Baek、Yong Jae Joo、Kwan Soo Kim

  DOI：10.1016/j.tetlet.2008.05.118

  日期：2008.8

  ve group on the galactosyl donor was essential for the α-galactosylation of secondary alcohol acceptors. The present method was successfully applied to the synthesis of di- and tetrasaccharide subunits of cell wall polysaccharides of Talaromyces flavus.

  已经建立了使用2'-羧基苄基糖苷作为半乳糖基供体的立体选择性α-半呋喃糖基化。半乳糖基供体上的四苄基保护基对于仲醇受体的α-半乳糖基化至关重要。本方法已成功地应用于合成了Talaromyces flavus细胞壁多糖的二糖和四糖亚基。
• Total Synthesis of Agelagalastatin
  作者：Yong Joo Lee、Bo-Young Lee、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1021/ol061444o

  日期：2006.8.1

  The total synthesis of agelagalastatin, an antineoplastic glycosphingolipid, has been achieved. The synthesis involved an alpha-selective glycosylation of the ceramide moiety with the trisaccharide fluoride. The trisaccharide component was constructed employing the CB glycoside method which permitted a completely alpha-stereoselective galactofuranosylation.