3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol | 887480-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol
• CAS: 887480-08-2
• 化学式: C₄₁H₄₄O₈
• 分子量: 664.796
• InChiKey: KSJIBMATSOJQQZ-VDQQNJLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.84
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 在 sodium tetrahydroborate 、 乙酸酐 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 35.0h， 生成 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-glucopyranosyl-(1->4)-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol
  参考文献：
  名称：

  Preparation of Building Blocks for Carba‐Oligosaccharides: Some Protected 5a′‐Carba‐D‐hexopyranosyl‐1,5‐anhydro‐2‐deoxy‐D‐arabino‐hex‐1‐enitols, and 5a,5a′‐Dicarba Congeners Thereof

  摘要：

  Four configurational types of two protected O -linked (5a-carba-D-hexopyranosyl)-D-glucal and carba-D-glucal derivatives were prepared in order to provide versatile synthetic intermediates readily convertible into carba-oligosaccharides of biological interest. These compounds may also find application as donors for elongation of carba-oligosaccharide chains having O -linked carbahexopyranose residues at nonreducing ends.

  DOI：

  10.1080/07328300600572907
• 作为产物：
  描述：

  2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以97%的产率得到3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol
  参考文献：
  名称：

  Preparation of Building Blocks for Carba‐Oligosaccharides: Some Protected 5a′‐Carba‐D‐hexopyranosyl‐1,5‐anhydro‐2‐deoxy‐D‐arabino‐hex‐1‐enitols, and 5a,5a′‐Dicarba Congeners Thereof

  摘要：

  Four configurational types of two protected O -linked (5a-carba-D-hexopyranosyl)-D-glucal and carba-D-glucal derivatives were prepared in order to provide versatile synthetic intermediates readily convertible into carba-oligosaccharides of biological interest. These compounds may also find application as donors for elongation of carba-oligosaccharide chains having O -linked carbahexopyranose residues at nonreducing ends.

  DOI：

  10.1080/07328300600572907

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。