isopropyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: isopropyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside
• 英文别名: [(4aR,6S,7R,8R,8aS)-7-hydroxy-2-phenyl-6-propan-2-ylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 9H-fluoren-9-ylmethyl carbonate
• 化学式: C₃₁H₃₂O₇S
• 分子量: 548.657
• InChiKey: WKGHKABUAPZNTO-QKDKHZFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isopropyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Facile Synthesis of Saponins Containing 2,3-Branched Oligosaccharides by Using Partially Protected Glycosyl Donors

  摘要：

  Two natural saponins 1 and 2, isolated from Solanum indicum L., and containing 2,3-branched sugar moieties, have been efficiently synthesized. Partially protected monosaccharide and disaccharide donors were used to facilitate target synthesis. Stereo factors were critical in incorporating 2,3-branched sugars on steroid aglycones. Saponin 1 was synthesized in five steps and 30% overall yield, while saponin 2 was obtained using six straightforward sequential reactions in 31% overall yield. Saponin 2 shows promising cytotoxic activity toward human hepatocellular carcinoma BEL-7402 with an IC50 of <6 mug/mL.

  DOI：

  10.1021/jo0493929
• 作为产物：
  描述：

  异丙基-beta-D-硫代半乳糖吡喃糖苷 在 吡啶 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 isopropyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  使用部分保护的糖基供体合成皂苷。

  摘要：

  [反应：见正文]在标准糖基化条件下研究了一类新的具有未保护的2-和2,4-羟基的糖基供体。已证明该方法通常对烷基和甾体糖苷的合成有效。利用这些部分保护的供体，通过四个简单的顺序反应，以35％的总收率制备了含有2,4-支链低聚糖的天然皂素。

  DOI：

  10.1021/ol035353s

文献信息

• Synthesis of Saponins Using Partially Protected Glycosyl Donors
  作者：Yuguo Du、Guofeng Gu、Guohua Wei、Yuxia Hua、Robert J. Linhardt

  DOI：10.1021/ol035353s

  日期：2003.10.1

  glycosylation conditions. This approach was shown to be generally effective for the synthesis of alkyl and steroidal glycosides. A natural saponin, containing 2,4-branched oligosaccharide, was prepared in 35% overall yield in four straightforward sequential reactions by taking advantage of these partially protected donors.

  [反应：见正文]在标准糖基化条件下研究了一类新的具有未保护的2-和2,4-羟基的糖基供体。已证明该方法通常对烷基和甾体糖苷的合成有效。利用这些部分保护的供体，通过四个简单的顺序反应，以35％的总收率制备了含有2,4-支链低聚糖的天然皂素。
• Facile Synthesis of Saponins Containing 2,3-Branched Oligosaccharides by Using Partially Protected Glycosyl Donors
  作者：Guofeng Gu、Yuguo Du、Robert J. Linhardt

  DOI：10.1021/jo0493929

  日期：2004.8.1

  Two natural saponins 1 and 2, isolated from Solanum indicum L., and containing 2,3-branched sugar moieties, have been efficiently synthesized. Partially protected monosaccharide and disaccharide donors were used to facilitate target synthesis. Stereo factors were critical in incorporating 2,3-branched sugars on steroid aglycones. Saponin 1 was synthesized in five steps and 30% overall yield, while saponin 2 was obtained using six straightforward sequential reactions in 31% overall yield. Saponin 2 shows promising cytotoxic activity toward human hepatocellular carcinoma BEL-7402 with an IC50 of <6 mug/mL.