2'-(benzyloxycarbonyl)benzyl 5,6-O-isopropylidene-β-D-galactofuranoside | 911371-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(benzyloxycarbonyl)benzyl 5,6-O-isopropylidene-β-D-galactofuranoside
• 英文别名: benzyl 2-[[(2R,3R,4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-yl]oxymethyl]benzoate
• CAS: 911371-43-2
• 化学式: C₂₄H₂₈O₈
• 分子量: 444.482
• InChiKey: DGKQUHNDOXNQOX-WKHGPKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-(benzyloxycarbonyl)benzyl 5,6-O-isopropylidene-β-D-galactofuranoside 在 咪唑 、 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 6.0h， 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 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 1.0h， 生成 2'-(benzyloxycarbonyl)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

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。
• Chemical Synthesis of Cyclic Galactooligofuranosides Isolated from Enzymatic Degradation Products of Cell Wall Arabinogalactan of <i>Mycobacterium tuberculosis</i>
  作者：Kwan Soo Kim、Bo-Young Lee、Sung Ho Yoon、Hyo Jin Jeon、Ju Yuel Baek、Kyu-Sung Jeong

  DOI：10.1021/ol800530u

  日期：2008.6.1

  Synthesis of cyclic tetra-, hexa- and octasaccharides containing alternating (1 -> 5)-,beta- and (1 -> 6)-beta-galactofuranosyl linkages has been achieved by intramolecular cycloglycosylation of corresponding linear sugars and by cyclooligomerization of 1,6-linked and 1,5-linked disaccharides. In particular,cyclooligornerization of the (1 -> 6)-beta-galactofuranosyl disaccharide provides an efficient way to secure all three cyclic sugars in one operation.
• 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.