[(2R,3S,4R,5R,6S)-4-benzoyloxy-5-(1,3-dioxoisoindol-2-yl)-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl] benzoate | 400020-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6S)-4-benzoyloxy-5-(1,3-dioxoisoindol-2-yl)-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl] benzoate
• CAS: 400020-10-2
• 化学式: C₃₄H₂₇NO₈S
• 分子量: 609.656
• InChiKey: DPONMPFMBXOARL-DNWRJOIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6S)-4-benzoyloxy-5-(1,3-dioxoisoindol-2-yl)-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl] benzoate 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 乙酰氯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 p-methoxyphenyl 3,4-di-O-benzoyl-6-O-(3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  A Synthetic Pentasaccharide with GTPase Activity

  摘要：

  [GRAPHICS]The design, synthesis, and preliminary evaluation of the first example of synthetic pentasaccharide (1) that shows marked rate enhancement and specificity for the hydrolysis of GTP to GDP and orthophosphate (OP) are reported. At the concentration ratios of GTP/1 = 3.6 and GTP/Mg2+ = 1 (pH 7.1, 50 degreesC), a rate enhancement of about 500-fold was obtained.

  DOI：

  10.1021/ol010257h
• 作为产物：
  描述：

  2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 在 4-二甲氨基吡啶 、 硫酸 作用下， 以 吡啶 、 甲醇 、 氯仿 为溶剂， 反应 23.0h， 生成 [(2R,3S,4R,5R,6S)-4-benzoyloxy-5-(1,3-dioxoisoindol-2-yl)-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl] benzoate
  参考文献：
  名称：

  A Synthetic Pentasaccharide with GTPase Activity

  摘要：

  [GRAPHICS]The design, synthesis, and preliminary evaluation of the first example of synthetic pentasaccharide (1) that shows marked rate enhancement and specificity for the hydrolysis of GTP to GDP and orthophosphate (OP) are reported. At the concentration ratios of GTP/1 = 3.6 and GTP/Mg2+ = 1 (pH 7.1, 50 degreesC), a rate enhancement of about 500-fold was obtained.

  DOI：

  10.1021/ol010257h

文献信息

• One-Pot Synthesis of Glucosamine Oligosaccharides
  作者：Micha Fridman、Dmitry Solomon、Shay Yogev、Timor Baasov

  DOI：10.1021/ol017054d

  日期：2002.1.1

  2-amino-2-deoxy glucose by selective introduction of different N-protecting (NPhth and NHTroc) and anomeric leaving groups (ethylthio and phenylthio) enabled highly efficient oligosaccharide synthesis in a one-pot manner. One-pot sequential glycosylation of three and four units of 2-amino-2-deoxy glucose gave trisaccharides and tetrasaccharide in 50-81% yields.

  [反应：见正文]通过选择性引入不同的N-保护基（NPhth和NHTroc）和异头离去基团（乙硫基和苯硫基）来调节衍生自2-氨基-2-脱氧葡萄糖的糖基供体的反应性，可实现高效的寡糖合成一锅法。一锅顺序糖基化的三个和四个单元的2-氨基-2-脱氧葡萄糖依次产生三糖和四糖，收率为50-81％。
• Iterative Glycosylation of 2-Deoxy-2-aminothioglycosides and Its Application to the Combinatorial Synthesis of Linear Oligoglucosamines
  作者：Shigeru Yamago、Takeshi Yamada、Tomokazu Maruyama、Jun-ichi Yoshida

  DOI：10.1002/anie.200353552

  日期：2004.4.13
• A Synthetic Pentasaccharide with GTPase Activity
  作者：Dmitry Solomon、Micha Fridman、Jeanwei Zhang、Timor Baasov

  DOI：10.1021/ol010257h

  日期：2001.12.1

  [GRAPHICS]The design, synthesis, and preliminary evaluation of the first example of synthetic pentasaccharide (1) that shows marked rate enhancement and specificity for the hydrolysis of GTP to GDP and orthophosphate (OP) are reported. At the concentration ratios of GTP/1 = 3.6 and GTP/Mg2+ = 1 (pH 7.1, 50 degreesC), a rate enhancement of about 500-fold was obtained.