2'-carboxybenzyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-(3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside | 911371-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-carboxybenzyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-(3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
• 英文别名: 2-[[(2S,4aR,6R,7R,8S,8aS)-8-[(2S,3R,4S,5S)-3-[(2R,3R,4S,5S)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3,4-bis(phenylmethoxy)oxolan-2-yl]oxy-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenylmethoxyoxolan-2-yl]oxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxymethyl]benzoic acid
• CAS: 911371-35-2
• 化学式: C₇₈H₈₂O₁₈
• 分子量: 1307.5
• InChiKey: ZHYLLMVFJGRQFE-WOZYTPLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  96
• 可旋转键数：
  30
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  185
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2'-carboxybenzyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-(3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 4 A molecular sieve 、 吡啶 、 氢氟酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-(3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl fluoride 、 (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-(3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl fluoride
  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-benzyl-α-D-galactofuranosyl)-(1->2)-(3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 在 palladium on activated charcoal 乙酸铵 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 以95%的产率得到2'-carboxybenzyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-(3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
  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.