allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside | 914097-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside
• 英文别名: (3aS,4R,6R,7R,7aS)-7-[(4-methoxyphenyl)methoxy]-4-(2-methoxypropan-2-yloxymethyl)-2,2-dimethyl-6-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 914097-72-6
• 化学式: C₂₄H₃₆O₈
• 分子量: 452.545
• InChiKey: CNIZANJYOFEAER-CDJZJNNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	allyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside	147221-63-4	C16H28O7	332.394
  ——	allyl β-D-galactopyranoside	2595-07-5	C9H16O6	220.222

反应信息

• 作为反应物：
  描述：

  allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 在 吡啶 、 三乙基硅烷 、 四(三苯基膦)钯 、 molecular sieve 、 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 allyl 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells

  摘要：

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.

  DOI：

  10.1021/ol062199b
• 作为产物：
  描述：

  allyl β-D-galactopyranoside 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells

  摘要：

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.

  DOI：

  10.1021/ol062199b

文献信息

• Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells
  作者：Chengfeng Xia、Dapeng Zhou、Chengwen Liu、Yanyan Lou、Qingjia Yao、Wenpeng Zhang、Peng George Wang

  DOI：10.1021/ol062199b

  日期：2006.11.1

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.