2-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione | 220911-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione
• 英文别名: 2-[(2S,3R,4R,5R,6R)-2-methylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 220911-65-9
• 化学式: C₃₆H₃₅NO₆S
• 分子量: 609.743
• InChiKey: LUOSFZVJOSSBSS-JNCMBMRBSA-N

物化性质

• 沸点：
  735.898±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.310±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  99.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  octyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 2-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 在 4 A molecular sieve 、 dimethyl(methylthio)sulfonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到2-[(3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  The 2-N,N-Dibenzylamino Group as a Participating Group in the Synthesis ofβ-Glycosides

  摘要：

  The novel glycosyl donor 2-N,N-dibenzylaminothioglycoside 1 reacts with glycopyranoside alcohols 2, presumably via intermediate 3, to provide 1,2-trans-linked disaccharides 4 in high yield (78-86 %) and with high stereoselectivity. The N-benzyl protecting groups are readily cleaved under normal hydrogenolysis conditions, facilitating the synthesis of oligosaccharides with free amino groups.

  DOI：

  10.1002/(sici)1521-3773(19990201)38:3<346::aid-anie346>3.0.co;2-l
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 在 sodium methylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 2-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione
  参考文献：
  名称：

  The 2-N,N-Dibenzylamino Group as a Participating Group in the Synthesis ofβ-Glycosides

  摘要：

  The novel glycosyl donor 2-N,N-dibenzylaminothioglycoside 1 reacts with glycopyranoside alcohols 2, presumably via intermediate 3, to provide 1,2-trans-linked disaccharides 4 in high yield (78-86 %) and with high stereoselectivity. The N-benzyl protecting groups are readily cleaved under normal hydrogenolysis conditions, facilitating the synthesis of oligosaccharides with free amino groups.

  DOI：

  10.1002/(sici)1521-3773(19990201)38:3<346::aid-anie346>3.0.co;2-l