2'-(benzyloxycarbonyl)benzyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranoside | 911371-47-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(benzyloxycarbonyl)benzyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranoside
• 英文别名: benzyl 2-[[(2R,3R,4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-4-phenylmethoxyoxolan-2-yl]oxymethyl]benzoate
• CAS: 911371-47-6
• 化学式: C₃₁H₃₄O₈
• 分子量: 534.606
• InChiKey: VBDZFZXXSGWHOQ-OVFYEYCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 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 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2'-(benzyloxycarbonyl)benzyl (2,3,5,6-tetra-O-benzyl-α-galactofuranosyl)-(1->2)-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-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

文献信息

• 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.